Day: January 4, 2023

Photochemistry of 3- and 5-Phenylisothiazoles. Competing Phototransposition Pathways was written by Pavlik, James W.;Tongcharoensirikul, Pakamas. And the article was included in Journal of Organic Chemistry in 2000.Synthetic Route of C9H7NS This article mentions the following:

5-Phenylisothiazole undergoes phototransposition via the electrocyclic ring closure-heteroatom migration pathway and by the N₂-C₃ interchange reaction pathway. The latter route is enhanced by the addition of triethylamine (TEA) to the reaction medium and by increasing the polarity of the solvent. In addition to phototransposition, 5-phenylisothiazole also undergoes photocleavage to 2-cyano-1-phenylethenethiol which was trapped by reaction with benzyl bromide to yield 2-cyano-1-phenylethen-1-yl benzyl thioether. 3-Phenylisothiazole also phototransposes by both reaction pathways, but the product distribution is not affected by the addition of TEA or by changing the solvent polarity. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Synthetic Route of C9H7NS

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

Selective Detection of 5-Formyl-2′-deoxyuridine, an Oxidative Lesion of Thymidine, in DNA by a Fluorogenic Reagent was written by Hirose, Wataru;Sato, Kousuke;Matsuda, Akira. And the article was included in Angewandte Chemie, International Edition in 2010.Formula: C9H10N2O2S This article mentions the following:

The authors report a new concept for the simple detection of 5-Formyl-2′-deoxyuridine (fodUrd) in damaged DNA with a fluorogenic reagent. The reagent 2-amino-4,5-dimethoxythiophenol (I) shows no fluorescence before reaction with the target fodUrd in DNA. However, upon the reaction of I with fodUrd, the formyl group at the 5-position of fodUrd is converted into a benzothiazol-2-yl group, which is directly conjugated with the uracil group. This ring system is similar to luciferin, which undergoes the luciferase reaction to produce luminescence. Thus, fodUrd in DNA could be detected directly by fluorescence measurement without enzymic hydrolysis of the target DNA to its corresponding nucleosides, HPLC separation, and anal. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Formula: C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C9H10N2O2S

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

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I₂/dimethyl sulfoxide as a catalytic oxidative system was written by Zhang, Qian;Wu, Jiefei;Pan, Zexi;Zhang, Wen;Zhou, Wei. And the article was included in Journal of Chemical Research in 2021.SDS of cas: 6318-74-7 This article mentions the following:

A series of 2-aminothiazoles was prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I₂/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus provided a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7SDS of cas: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.SDS of cas: 6318-74-7

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

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands was written by Mishra, Nidhi;Singh, Anoop S.;Agrahari, Anand K.;Singh, Sumit K.;Singh, Mala;Tiwari, Vinod K.. And the article was included in ACS Combinatorial Science in 2019.Product Details of 1843-21-6 This article mentions the following:

D-Glucose-derived triazoles such as I were prepared for use as ligands in coupling and tandem coupling and cyclization reactions using CuI as catalyst and K₂CO₃ in DMF to yield benzoxazoles, benzothiazoles, benzimidazoles, arylaminobenzothiazoles, and benzimidazoquinazolinones. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Product Details of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Product Details of 1843-21-6

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

Structure of sulfonic acids of 2-amino-4-methylthiazole was written by Postovskii, I. Ya.;Mamykina, T. S.. And the article was included in Zhurnal Obshchei Khimii in 1953.Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Ochiai and Nagasawa, C.A. 33, 7782.9; Hurd, et al., C.A. 45, 155e. ClSO₃H with 2-acetamido-4-methylthiazole (I) yields 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (II). The structures proposed by Hurd and Ochiai (loc. cit.) are erroneous. The acid (III), m. 253-6°, formed by hydrolysis of II and on heating with H₂SO₄ changes to an acid, decomposing above 340°, an example of an unusual transition of the sulfonic acid into a sulfamic acid (IV or IVa). Addition of ClSO₃H to I in CCl₄ gives some 40% pure III, m. 256° (decomposition). The following technique gives better results. I (17.5 g.) in 75 ml. CCl₄ was slowly added with cooling over 3 hrs. to 22 ml. ClSO₃H (temperature kept under 14°), and the mixture poured on ice, yielding 79% III, decompose 253-6° (from H₂O). I (20 g.) added to 30 ml. concentrated H₂SO₄, and the mixture heated 5 hrs. at 150-65°, cooled to 50°, and poured into ice water gave 76% IV (or IVa), m. above 350° (from H₂O). III taken up in aqueous NaOH, the solution evaporated, and the resulting Na salt (7.7 g.) treated with 17 ml. Ac₂O, refluxed 2 hrs., and cooled gave 8.8 g. Ac derivative, which, heated 1-1.5 hrs. with 15 g. PCl₅ on a steam bath, cooled, and treated with ice, gave II, m. 156-7° (from CCl₂:CHCl), identical with the specimen obtained from ClSO₃H and I directly. II also forms from ClSO₃H and the Na salt of III, but the yield is lower. I contains 1 active H/(Zerevitinov) mol. II (2.5 g.) added to 1.2 g. EtNHPh in dry pyridine, kept 1 day, and diluted with H₂O gave 91% of the corresponding N-ethylanilide, m. 188-9° (from dilute EtOH). This with Me₂SO₄ in N NaOH gave 74% methylated product, probably (V) or (VA), m. 128-9°, which does not react with MeMgI, indicating the absence of active H. Thus the ethylanilide must have structure (VI). II in dry pyridine treated with cooling with gaseous Me₂NH gave 93% 2-acetamido-N,N,4-trimethyl-5-thiazolesulfonamide, m. 242-3° (from dilute EtOH), which has 1 active H, at the AcNH group. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Name: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Chemical constitution and fungistatic action of organic sulfur compounds was written by Davies, W. H.;Sexton, W. A.. And the article was included in Biochemical Journal in 1946.Computed Properties of C13H10N2S This article mentions the following:

The test organisms were Fusarium graminearum Schwabe and Penicillium digitatum Sacc., results being reported with reference to the latter. Compounds tested include metal xanthates, ROCS₂M (M = Na, K, Ni, Zn; R = Me, Et, Bu, iso-Bu, Am, dodecyl); Me, Et, and Bu derivatives of (ROCS)₂S and (ROCSS)₂; tetramethyl- and tetraethylthiuram monosulfides; thiuram disulfides, (RR’NCSS)₂ (R,R’ = H; R = H, R’ = Me; R,R’ = Me; R,R’ = Et; R = Ph, R’ = Me; R,R’ = (CH₂)₅); Me, Bu, PhCH₂, 2-hydroxyethyl, allyl dimethyldithiocarbamates; Me, Et, and PhCH₂ esters of diethyl-, dicyclohexyl-, pentamethylene-, and phenyldithiocarbamic acids; Me, Et, Pr, iso-Pr, Bu, iso-Bu, dodecyl phenylthiocarbamates; Me p-tolylthiocarbamate and (p-chlorophenyl)thiocarbamate; Et, Bu, Ph, o-, m-, and p-carboxy-, p-hydroxy-, p-acetoxy-, p-amino-, p-acetylamino-, p-dimethylamino-, and p-chlorophenyl thiocyanates; Et, Bu, allyl, Ph, p-tolyl, and p-chloro-, p-methoxy-, m-carboxy-, p-carboxy-, p-hydroxy-, p-acetoxy-, m-acetoxy-, 4-hydroxy-2,6-dimethyl-, 3-chloro-4-hydroxy-, 3-methyl-4-hydroxyphenyl isothiocyanates; 1-HO, 1-HS, 1-MeS, 1-EtS, 1-PrS, 1-HOCH₂CH₂S, 4-Cl-1-HS, 4-Cl-1-MeS, 5-EtO-1-HS, 5-O₂N-1-HS, 1-H₂N, 1-MeNH, 1-PhNH, 5-EtO-1-H₂N, 1-NCS derivatives of benzothiazole (in this series, the last-named compound was the most active); and the disulfide of 1-mercaptobenzothiazole. The lower xanthates and hydroxyaryl isothiocyanates were the most active compounds, the activity of the latter being equal to that of PhHgOAc, but short of that of EtHgCl. The replacement of S by O in some phenylthiocarbamates and (ROCS)₂S compounds did not affect the activity materially. New compounds were: dimethyldithiocarbamates: Bu, b₂₀ 157-9°, PhCH₂, b₂₀ 220°, m. 40-1°, 2-hydroxyethyl, “undistillable liquid,” allyl, b₂₀ 140°; Me pentamethylenedithiocarbamate, b₁₀ 164-6°, m. 31-2°; tetraethylthiuram monosulfide, m. 33-4°; m-carboxyphenyl thiocyanate, m. 177-9° (decomposition); p-carboxyphenyl thiocyanate, m. 220-1° (decomposition); 3-methyl-4-hydroxyphenyl isothiocyanate, b₃ 146-9°, m. 52-4°; 3-chloro-4-hydroxyphenyl isothiocyanate, m. 58-9°. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Computed Properties of C13H10N2S

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

One-pot three-component protocol for the synthesis of substituted 2-aminothiazoles was written by Guo, Shanshan;Zhao, Donghong;Zhu, Yue;Yu, Yongping;Chen, Wenteng;Zhang, Guolin. And the article was included in Synthetic Communications in 2017.Recommanded Product: 6318-74-7 This article mentions the following:

Substituted 2-aminothiazoles have been synthesized from α-nitro-epoxides, cyanamide, and sodium sulfide through a facile, three-component, and ecofriendly protocol with good to excellent yields [e.g., nitro epoxide I + cyanamide + Na₂S.9H₂O → thiazole II (up to 88%)]. This reaction was achieved at room temperature without any additives. A possible mechanism has also been proposed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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: 6318-74-7

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

Further SAR on the (Phenylsulfonyl)piperazine Scaffold as Inhibitors of the Aedes aegypti Kir1 (AeKir) Channel and Larvicides was written by Aretz, Christopher D.;Kharade, Sujay V.;Chronister, Keagan;Rusconi Trigueros, Renata;Martinez Rodriguez, Erick J.;Piermarini, Peter M.;Denton, Jerod S.;Hopkins, Corey R.. And the article was included in ChemMedChem in 2021.Safety of Thiazol-2-ylmethanamine This article mentions the following:

Zika virus (ZIKV), dengue fever (DENV) and chikungunya (CHIKV) are arboviruses that are spread to humans from the bite of an infected adult female Aedes aegypti mosquito. As there are no effective vaccines or therapeutics for these diseases, the primary strategy for controlling the spread of these viruses is to prevent the mosquito from biting humans through the use of insecticides. Unfortunately, the commonly used classes of insecticides have seen a significant increase in resistance, thus complicating control efforts. Inhibiting the renal inward rectifier potassium (Kir) channel of the mosquito vector Aedes aegypti has been shown to be a promising target for the development of novel mosquitocides. We have shown that Kir1 channels play key roles in mosquito diuresis, hemolymph potassium homeostasis, flight, and reproduction Previous work from our laboratories identified a novel (phenylsulfonyl)piperazine scaffold as potent AeKir channel inhibitors with activity against both adult and larval mosquitoes. Herein, we report further the synthesis and SAR work around this scaffold and have identified addnl. compounds, e.g., I and II, with improved in vitro potency and mosquito larvae toxicity. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Safety of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Safety of Thiazol-2-ylmethanamine

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

Inhibitors for penicillinase was written by Behrens, Otto K.;Garrison, Lynette. And the article was included in Archives of Biochemistry in 1950.SDS of cas: 55661-33-1 This article mentions the following:

One of the mechanisms by which bacteria overcome or prevent the inhibitory action of penicillin (I) involves penicillinase (II) which forms penicilloic acid. Hence, inhibitors for II might be capable of extending the antibiotic action of I to some organisms not susceptible to the antibiotic. Tests on anti-II activity have been performed manometrically (cf. C.A. 43, 3489i) with compounds structurally related to a portion of the I mol. 2-Benzylimidazole (III), 2-methylimidazole (IV), 2-aminomethylthiazole (V), benzylpenicillic acid, p-chlorobenzoyl-DL-seryl-DL-valine, histamine, 2-propyl-4-thiazolidinecarboxylic acid, pencillamine (VI), thiolthreonine and cysteine exhibited marked anti-II activity. When certain of these compounds were tested for their ability to enhance the effectiveness of I on a II-producing organism, their efficacy did not parallel that in the anti-II test. VI markedly potentiated the activity of I but III, IV, and V had little or no effect. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1SDS of cas: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.SDS of cas: 55661-33-1

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

Effect of various factors on the reaction of 2-aminobenzothiazoles with propylene oxide was written by Ambartsumova, R. F.;Kosmacheva, L. P.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) in 2002.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The authors have shown that when 2-substituted 2-aminobenzothiazoles react with propylene oxide in proton-donor solvents, products of hydroxyalkylation of both the heterocycle and o-aminothiophenol formed as a result of its cleavage are synthesized. The authors have traced the effect of the nature of the solvent, various additives, the reaction temperature, and the heating time on this process. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Name: N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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