Jagadeesh, Rajenahally V. et al. published their research in ACS Catalysis in 2015 | CAS: 2942-06-5

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Category: thiazole

Nitrogen-Doped Graphene-Activated Iron-Oxide-Based Nanocatalysts for Selective Transfer Hydrogenation of Nitroarenes was written by Jagadeesh, Rajenahally V.;Natte, Kishore;Junge, Henrik;Beller, Matthias. And the article was included in ACS Catalysis in 2015.Category: thiazole This article mentions the following:

Nanoscaled iron oxides on carbon were modified with nitrogen-doped graphene (NGr) and found to be excellent catalysts for the chemoselective transfer hydrogenation of nitroarenes to anilines. Under standard reaction conditions, a variety of functionalized and structurally diverse anilines, which serve as key building blocks and central intermediates for fine and bulk chems., were synthesized in good to excellent yields. In the experiment, the researchers used many compounds, for example, 6-Nitrobenzothiazole (cas: 2942-06-5Category: thiazole).

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Yang, Yeguo et al. published their research in Oncology Reports in 2016 | CAS: 222716-34-9

3-(Benzo[d]thiazol-2-yl)-6-ethyl-7-hydroxy-8-(piperidin-1-ylmethyl)-4H-chromen-4-one (cas: 222716-34-9) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Formula: C24H24N2O3S

Skp2 is associated with paclitaxel resistance in prostate cancer cells was written by Yang, Yeguo;Lu, Yi;Wang, Lihui;Mizokami, Atsushi;Keller, Evan T.;Zhang, Jian;Fu, Jiejun. And the article was included in Oncology Reports in 2016.Formula: C24H24N2O3S This article mentions the following:

Prostate cancer is the most commonly diagnosed tumor in men in the United States. Patients with hormone refractory prostate cancer are often treated with paclitaxel, but most of them eventually develop drug resistance. S-phase kinase associated protein 2 (Skp2) is a component of the SCF (Skp1-Cullin1-F-box) type of E3 ubiquitin ligase complexes. In the present study, we investigated the role of Skp2 in paclitaxel-resistant DU145-TxR or PC-3-TxR cells by Skp2 silencing or using Skp2 inhibitors. We first confirmed that Skp2 expression is upregulated in DU145-TxR or PC-3-TxR cells compared with their parental cells DU145 or PC-3, resp. Knockdown of Skp2 or Skp2 inhibitor treatment in DU145-TxR or PC-3-TxR cells restored paclitaxel sensitivity. E-cadherin was decreased while Vimentin was increased in PC-3-TxR or DU145-TxR cells. In addition, p27 expression was inversely correlated with Skp2 expression in DU145-TxR or PC-3-TxR cells. Moreover, p27 was found to increase in both Skp2 silencing PC-3-TxR and DU145-TxR cells. These results suggest that Skp2 is associated with prostate cancer cell resistance to paclitaxel. Skp2 may be a potential therapeutic target for drug-resistant prostate cancer. In the experiment, the researchers used many compounds, for example, 3-(Benzo[d]thiazol-2-yl)-6-ethyl-7-hydroxy-8-(piperidin-1-ylmethyl)-4H-chromen-4-one (cas: 222716-34-9Formula: C24H24N2O3S).

3-(Benzo[d]thiazol-2-yl)-6-ethyl-7-hydroxy-8-(piperidin-1-ylmethyl)-4H-chromen-4-one (cas: 222716-34-9) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Formula: C24H24N2O3S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Qiu, Shaozhong et al. published their research in Advanced Synthesis & Catalysis in 2018 | CAS: 3034-53-5

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Category: thiazole

One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)-Copper(I) Iodide-Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction was written by Qiu, Shaozhong;Zhang, Caiyang;Qiu, Rui;Yin, Guodong;Huang, Jinkun. And the article was included in Advanced Synthesis & Catalysis in 2018.Category: thiazole This article mentions the following:

The low loading combination of the complex [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand-free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single-step procedure. The unsym. diarylalkynes can be obtained through a one-pot two-step approach. The reactions of aryl bromides with 1,4-bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4-diaryl-1,3-diynes in a similar fashion. This route to diarylalkynes and 1,4-diaryl-1,3-diynes is complementary to previously reported synthetic procedures. In the experiment, the researchers used many compounds, for example, 2-Bromothiazole (cas: 3034-53-5Category: thiazole).

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

de Alexandre Sebastiao, Fernanda et al. published their research in Aquaculture International in 2022 | CAS: 14769-73-4

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

Evaluation of the clinical safety and efficacy of fenbendazole and levamisole in the control of Neoechinorhynchus buttnerae in Colossoma macropomum – Acanthocephalosis treatments was written by de Alexandre Sebastiao, Fernanda;Souza Rocha, Maria Juliete;Rodrigues Brandao, Franmir;Braga de Oliveira, Maria Ines;de Melo Souza, Damy Caroline;Carlos do Nascimento Barbosa, Bruna;Castro Monteiro, Patricia;Majolo, Claudia;Crescencio, Roger;Tavares-Dias, Marcos;Campos Chagas, Edsandra. And the article was included in Aquaculture International in 2022.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole This article mentions the following:

Abstract: Occurrences of parasitic infections caused by Neoechinorhynchus buttnerae in Colossoma macropomum (tambaqui), especially in the northern region of Brazil, have increased in the past two decades and have caused economic losses in tambaqui production The aim of this study was to evaluate the in vivo efficacy and clin. safety of fenbendazole and levamisole in controlling and treating N. buttnerae in tambaqui for 30 days. Juvenile tambaqui naturally infected with N. buttnerae were distributed in 15 tanks (n = 12 per 1,000 L-tank), constituting five treatments, in triplicate. Treatments were administered via diet (mg kg-1 of live weight): control (0 mg kg-1), F1 (100 mg kg-1 of fenbendazole), F2 (200 mg kg-1 of fenbendazole), L1 (200 mg kg-1 of levamisole), and L2 (300 mg kg-1 of levamisole). Fish survival rate was 100during the entire exptl. period. Fenbendazole treatments were not effective against N. buttnerae; however, L1 and L2 showed efficacy of 73.4 and 99.15, resp. Treatments with fenbendazole or levamisole did not affect the growth parameters of tambaqui. F1 and F2 showed significant reduction in the hematocrit values when compared to L1, and Hb values were significantly reduced in F1 when compared to L1, L2, and the control group. There were no significant differences in RBC, MCV, and CHCM. The plasma glucose value was statistically lower in F1 than in the L1 (p = 0.03) and L2 (p = 0.02) treatments. For alanine aminotransferase, there was a significant reduction (p = 0.004) in the F1 and F2 groups compared to the L2 group. No statistical difference was observed for aspartate aminotransferase among the treatments. More studies are warranted to further evaluate other therapeutic strategies using shorter periods for controlling and efficiently treating N. buttnerae. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Khalili, Dariush et al. published their research in Applied Organometallic Chemistry in 2018 | CAS: 16112-21-3

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Recommanded Product: 2-(4-Methylphenyl)benzothiazole

2-Arylation/alkylation of benzothiazoles using superparamagnetic graphene oxide-Fe3O4 hybrid material as a heterogeneous catalyst with diisopropyl azodicarboxylate (DIAD) as an oxidant was written by Khalili, Dariush;Etemadi-Davan, Elham;Banazadeh, Ali Reza. And the article was included in Applied Organometallic Chemistry in 2018.Recommanded Product: 2-(4-Methylphenyl)benzothiazole This article mentions the following:

In this report, we introduced Graphene oxide-iron oxide (GO-Fe3O4) nanocomposites as a heterogeneous catalyst for arylation/alkylation of benzothiazoles with aldehydes and benzylic alcs. in the presence of diisopropyl azodicarboxylate (DIAD) as an oxidant which exclusively produced 2-aryl (alkyl)-1H-benzothizoles in moderate to excellent yields. The absence of precious metals and toxic solvent, easy product isolation, and recyclability of the GO-Fe3O4 with no loss of activity are notable advantages of this method. In the experiment, the researchers used many compounds, for example, 2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3Recommanded Product: 2-(4-Methylphenyl)benzothiazole).

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Recommanded Product: 2-(4-Methylphenyl)benzothiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Huang, Haigen et al. published their research in Applied Catalysis, A: General in 2018 | CAS: 2942-06-5

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Computed Properties of C7H4N2O2S

N-doped graphitic carbon-improved Co-MoO3 catalysts on ordered mesoporous SBA-15 for chemoselective reduction of nitroarenes was written by Huang, Haigen;Liang, Xiangcheng;Wang, Xueguang;Sheng, Yao;Chen, Chenju;Zou, Xiujing;Lu, Xionggang. And the article was included in Applied Catalysis, A: General in 2018.Computed Properties of C7H4N2O2S This article mentions the following:

Metallic Co-MoO3 catalysts supported on ordered mesoporous SBA-15 were first prepared through in situ reaction of SBA-15-supported Co-Mo oxides with 1,10-phenanthroline. The resulting Co-MoO3/NC@SBA-15 catalysts with N-doped carbon (NC) exhibited high catalytic activity and chemoselectivity for selective reduction of various functionalized nitroarenes to the corresponding arylamines in ethanol with hydrazine hydrate at near room temperature (30掳). For reduction of all tested substrates (28 examples), the catalyst could afford a conversion of >99% and arylamine selectivity of >99%. The excellent catalytic performance of the Co-MoO3/NC@SBA-15 was attributed to the Co-N(C)-Mo active sites generated through the interaction between the surface Co-N(C) and MoO3 species, promoting the dissociation of hydrazine mol. into the active H* species for the reduction of nitro groups. After the seventh cycle for reduction of 4-methoxylnitrobenzene, the 2%Co-MoO3/NC@SBA-15 showed little change in catalytic performance, textural properties, size and dispersion of metal species and valence states of elements, indicating high stability and recyclability. In the experiment, the researchers used many compounds, for example, 6-Nitrobenzothiazole (cas: 2942-06-5Computed Properties of C7H4N2O2S).

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Computed Properties of C7H4N2O2S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Bathula, Surendra Bose et al. published their research in Asian Journal of Chemistry in 2018 | CAS: 16112-21-3

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Synthetic Route of C14H11NS

Chitosan-SO3H: a green approach to 2-aryl/heteroaryl benzothiazoles under solvent-free conditions at room temperature was written by Bathula, Surendra Bose;Khagga, Mukkanti;Venkatasubramanian, Hariharakrishnan. And the article was included in Asian Journal of Chemistry in 2018.Synthetic Route of C14H11NS This article mentions the following:

An efficient green protocol was developed for the synthesis of 2-aryl/heteroaryl benzothiazoles by intramol. cyclocondensation of 2-mercaptoaniline with aryl/heteroaryl aldehydes using chitosan-SO3H as an efficient biocompatible and reusable heterogenous solid acid catalyst in presence of air under solvent free conditions at room temperature In the experiment, the researchers used many compounds, for example, 2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3Synthetic Route of C14H11NS).

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Synthetic Route of C14H11NS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Pal, R. et al. published their research in Xenobiotica in 1982 | CAS: 20485-41-0

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Reference of 20485-41-0

Thiomethylation and thiohydroxylation – a new pathway of metabolism of heterocyclic compounds was written by Pal, R.;Spiteller, G.. And the article was included in Xenobiotica in 1982.Reference of 20485-41-0 This article mentions the following:

Gas-liquid chromatog.-mass spectral anal. of thin-layer chromatog. fractions of urine samples from patients treated with clomethiazole (I) [533-45-9] revealed 2 minor metabolites formed by thiomethylation and thiohydroxylation, namely 2-methylthioclomethiazole聽聽[87764-52-1] and 5-acetyl-4-methyl-2-methylmercaptothiazole聽聽[73548-99-9], resp. The structures of 6 other minor metabolites resulting from side-chain degradation were also elucidated. The occurrence of metabolites with substituents at position 2 of the heterocyclic nucleus was assumed to be initiated by oxidative attack of the N, followed by nucleophilic substitution at position 2. In the experiment, the researchers used many compounds, for example, 4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0Reference of 20485-41-0).

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Reference of 20485-41-0

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Jafari, Behzad et al. published their research in ChemistrySelect in 2019 | CAS: 615-20-3

2-Chlorobenzothiazole (cas: 615-20-3) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 2-Chlorobenzothiazole

Synthesis of 2-Alkynyl- and 2-Amino-12H-benzothiazolo[2,3-b]quinazolin-12-ones and Their Inhibitory Potential against Monoamine Oxidase A and B was written by Jafari, Behzad;Jalil, Saquib;Zaib, Sumera;Safarov, Sayfidin;Khalikova, Muattar;Khalikov, Djurabay;Ospanov, Meirambek;Yelibayeva, Nazym;Zhumagalieva, Shynar;Abilov, Zharylkasyn A.;Turmukhanova, Mirgul Z.;Kalugin, Sergey N.;Salman, Ghazwan Ali;Ehlers, Peter;Hameed, Abdul;Iqbal, Jamshed;Langer, Peter. And the article was included in ChemistrySelect in 2019.Recommanded Product: 2-Chlorobenzothiazole This article mentions the following:

The 2-alkynyl- and 2-aminobenzothiazolo[2,3-b]quinazolin-12-ones I (R = isopropylaminyl, diphenylaminyl, morpholin-4-yl, etc.) and II (Ar = Ph, 4-tert-butylphenyl, naphthalen-1-yl, etc.) have been synthesized by Palladium catalyzed Buchwald-Hartwig and Sonogashira reactions. Synthesized derivatives were further evaluated for their role as potential inhibitors of monoamine oxidase A and B (MAO-A and B) isoenzymes. Most compounds possess moderate to excellent inhibitory potential against MAO-A and MAO-B. The 2-amino-substituted derivatives show a significantly higher activity as compared to 2-alkynyl- and previously reported 2-aryl derivatives Studied compounds might be employed as novel monoamine oxidase inhibitors and may provide insights for the development of new drug candidates against neurol. diseases. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole (cas: 615-20-3Recommanded Product: 2-Chlorobenzothiazole).

2-Chlorobenzothiazole (cas: 615-20-3) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 2-Chlorobenzothiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Childress, Scott J. et al. published their research in Journal of the American Chemical Society in 1951 | CAS: 7464-11-1

5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine (cas: 7464-11-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Computed Properties of C6H3Cl2N3S

Thiazolopyrimidines was written by Childress, Scott J.;McKee, R. L.. And the article was included in Journal of the American Chemical Society in 1951.Computed Properties of C6H3Cl2N3S This article mentions the following:

The synthesis of the thiazolo[5,4-d]pyrimidines of Weidel and Niemilowicz [Monatsh. 16, 721(1895)], and of Fischer and Ach [Ann. 288, 157(1895)] was extended. The previously reported synthesis of these compounds (Erlenmeyer and Furger, C.A. 41, 5133e) is unreliable. 6-Thiouramil (I) in 20 cc. 85% HCO2H refluxed 4 hrs., and the product cooled, filtered, dissolved in 35 cc. hot NH4OH, and precipitated with hot dilute HCl yielded 0.9 g. thiazolo[5,4-d]pyrimidine-5,7-diol (II), did not m. below 360掳. I (1.5 g.) and 15 g. Bz2O heated 3 hrs. on a steam bath and 30 min. at 170掳 and the product diluted with Et2O yielded 2.0 g. 2-Ph derivative of II, m. well above 360掳 (decomposition) (from 50% AcOH). II (0.5 g.) and 5 g. POCl3 heated 12 hrs. at 200掳, and the product cooled and poured over 30 g. ice, filtered, recrystallized from MeOH, and sublimed in vacuo yielded 0.15 g. 5,7-dichlorothiazolo[5,4-d] pyrimidine (III), m. 148.5-9.5掳. The 2-Me derivative (IIIA) of II (3 g.) and 50 g. POCl3 at 170掳 yielded 2.7 g. 2-Me derivative (IV) of III, white crystals, m. 109-10掳. IV (1 g.) and 15 cc. concentrated NH4OH heated 4 hrs. at 155掳, and the product chilled and filtered yielded (from 5 combined runs) 1.2 g. 5,7-diamino analog (V), of IV, white crystals from MeOH, m. 255-7掳. V has been submitted for pharmacol. evaluation. Di-Et 4,5-thiazoledicarboxylate (15 g.) and 40 cc. NH4OH yielded 9 g. 4,5-thiazoledicarboxamide (VI), white crystals from water, m. 298-300掳 (decomposition). Di-Et 2-methyl-4,5-thiazoledicarboxylate (VIA) (8 g.) and 20 cc. concentrated NH4OH yielded 4 g. 2-methyl-4,5-thiazoledicarboxamide (VII), white crystals from 50% EtOH, m. 296掳 (decomposition). Di-Et 2-phenyl-4,5-thiazoledicarboxylate (3 g.) yielded 2.5 g. diamide (VIII), white crystals from AcOH, m. 319-21掳. Br (1.8 g.) in 28 cc. water at 0掳 containing 3.6 g. KOH added to 2 g. VI, the mixture stirred 3 hrs. at 0掳 with addition of HOBr at intervals, the solution refrigerated overnight, filtered, heated 20 min. at 80掳, and the product precipitated with AcOH yielded 1.3 g. thiazolo[4,5-d]pyrimidine-5,7-diol (IX), did not m. below 360掳. IX (1.5 g.) and 30 g. PCl5 heated 12 hrs. at 200掳, the product added to 200 g. ice, and the solid filtered off and sublimed in vacuo yielded 0.2 g. product, m. 155-65掳; the filtrate made alk. with NH3 and the light yellow needles sublimed in vacuo yielded 0.7 g. 6-amino-2,4,5-trichloropyrimidine (X), white crystals, m. 170-1.5掳. X (0.7 g.) and 10 cc. concentrated NH4OH treated overnight at 100掳, chilled, filtered, the solid leached with hot EtOH, and the residue crystallized from EtO yielded a small amount of 4,6-diamino-2,5-dichloropyrimidine, m. 299-300掳; the alc.-soluble portion yielded 0.3 g. 2,4,6-triamino-5-chloropyrimidine, m. 197-9掳 (from water). VII (2 g.) treated with HOBr yielded 1.7 g. 2-methylthiazolo[4,5-d]pyrimidine-5,7-diol (XA), did not m. below 360掳. VIII (1.8 g.) treated with 56 cc. KOBr did not completely dissolve; the yield was 0.5 g. of the 2-Ph analog of XA, light-cream crystals, m. 331-2掳 (from 50% AcOH). VIA (1 g.) and 5 cc. 85% N2H4.H2O kept 1 hr. in 10 cc. EtOH at room temperature yielded the dihydrazide. VIA (7 g.) in 50 cc. EtOH and 5.3 g. 85% N2H4.H2O heated 48 hrs. at 100掳 and 30 min. at 140掳 yielded 2 g. 2-methylthiazolo-[4,5-d]pyridazine-4,7-diol, pale yellow powder from AcOH and from water, darkened slightly above 300掳, m. 355掳 (decomposition). IIIA (0.7 g.) refluxed with 10 g. BzH and 1 g. ZnCl2 yielded 0.3 g. 2-styrylthiazolo[5,4-d]pyrimidine-5,7-diol (XI), did not m. below 360掳; XA (0.7 g.) yielded 0.3 g. [4,5-d] isomer of XI, yellow powder, m. 329-31掳 (decomposition). In the experiment, the researchers used many compounds, for example, 5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine (cas: 7464-11-1Computed Properties of C6H3Cl2N3S).

5,7-Dichloro-2-methylthiazolo[5,4-d]pyrimidine (cas: 7464-11-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Computed Properties of C6H3Cl2N3S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica