Category: thiazole

The discovery of N-(1,3-thiazol-2-yl)pyridin-2-amines as potent inhibitors of KDR kinase was written by Bilodeau, Mark T.;Rodman, Leonard D.;McGaughey, Georgia B.;Coll, Kathleen E.;Koester, Timothy J.;Hoffman, William F.;Hungate, Randall W.;Kendall, Richard L.;McFall, Rosemary C.;Rickert, Keith W.;Rutledge, Ruth Z.;Thomas, Kenneth A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Product Details of 329794-40-3 This article mentions the following:

An azo-dye lead was modified to a N-(1,3-thiazol-2-yl)pyridin-2-amine series of KDR kinase inhibitors through the use of rapid analog libraries. The two lead compounds were N-butyl-N,3-dimethyl-4-[(5-nitro-2-thiazolyl)azo]benzenamine and N-(5-phenyl-2-thiazolyl)benzamide. This class has been found to be potent, selective, and of low mol. weight Mol. modeling has postulated an interesting conformational preference and binding mode for these compounds in the active site of the enzyme. A binding mode was proposed for the lead compound N-(5-phenyl-2-thiazolyl)-2-pyridinamine (I) in the KDR kinase active site. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Product Details of 329794-40-3).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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.Product Details of 329794-40-3

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

Synthesis of α-phosphoramidate containing benzothiazole group was written by Xu, Xue-li;Song, Wei;Gao, Wei-xia. And the article was included in Huaxue Shiji in 2014.SDS of cas: 68867-17-4 This article mentions the following:

This work is designed to use 3-nitro-4-thiosalicylic acid as the substrate, which was taken to cyclization, esterification, reduction, oxidation and the addition reactions, it was 6 steps in all. 14α-Phosphoramidates e. g., I, which contained benzothiazole groups were synthesized. And the products were confirmed by m.p., NMR, MS and IR. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4SDS of cas: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.SDS of cas: 68867-17-4

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

Design, synthesis, and biological evaluation of 2-substituted ethenesulfonic acid ester derivatives as selective PTP1B inhibitors was written by Liu, Jingbao;Deng, Xinxian;Jin, Yan;Xu, Buzhe;Liu, Wenlu;Jiang, Faqin;Fu, Lei. And the article was included in Pharmazie in 2015.COA of Formula: C15H12N2S This article mentions the following:

Fifteen 2-substituted ethenesulfonic acid ester derivatives were designed, synthesized, and evaluated for the inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and T-Cell protein tyrosine phosphatase (TCPTP). The structural activity relationship (SAR) of these compounds were discussed to clarify the impact of the linker and the optimized tail on the inhibitory activity of PTP1B and selectivity over TCPTP. Most of the compounds exhibited excellent inhibitory activities against PTP1B with IC₅₀ values of 1.5-8.9 μM. SAR anal. revealed that the substituents at the hydrophobic tail significantly alter the inhibitory activity against PTP1B and selectivity over TCPTP, e.g. compound Ethyl-2-(4-(3-(4-(2-chlorophenyl)thiazol-2-ylamino)propoxy)phenyl)ethenesulfonate showed excellent inhibitory activity to PTP1B with IC₅₀ = 7.8 μM, and ∼6-fold selectivity over TCPTP. Combined with our previous findings, that the linker length and the substituted hydrophobic tail had decisive influence on the PTP1B inhibitory activity and selectivity was confirmed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7COA of Formula: C15H12N2S).

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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.COA of Formula: C15H12N2S

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

Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles was written by Dondoni, Alessandro;Merchan, Francisco L.;Merino, Pedro;Rojo, Isabel;Tejero, Tomas. And the article was included in Synthesis in 1996.Formula: C4H6N2S This article mentions the following:

A method for the enantioselective synthesis of (aminoalkyl)thiazoles I (R = PhCH₂, allyl,cyclohexylmethyl, Me, 4-ClC₆H₄CH₂) via stereoselective alkylation of the imines of (+)-(R)-camphor or (-)-(1S,2S,5S)-2-hydroxy-3-pinanone and 2-thiazolemethanamine is described. Compounds I served as α-amino aldehyde precursors via thiazolyl-to-formyl conversion. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: C4H6N2S).

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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Formula: C4H6N2S

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

Synthesis of 2-amino-4,5-diphenylthiazoles was written by Liu, Wei-wei;Huo, Yun-feng;Zhang, Qiang;Li, Qu-xiang;Wu, Jun;Fang, Qun. And the article was included in Huaxue Shiji in 2014.Electric Literature of C15H12N2S This article mentions the following:

Five 2-hydroxy-1,2-diarylenthanones were synthesized by benzoin condensation with aromatic aldehydes as raw material and the reaction conditions were investigated. The optimized conditions are: n(catalyst) = 20 mol%, n(NaOH) = 10 mol%, and V(H₂O) : V(C₂H₅OH) = 1 : 3 as reagent. The 2-amino-4,5-diarylthiazoles I(R = H, 4-Me, 4-MeO, 2-MeO, 4-Cl, 2-Cl) were synthesized from 2-hydroxy-1,2-diary lenthanones by a two-step reaction of chlorination and cyclization. The structures of were confirmed by IR, ¹HNMR and HRMS. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Electric Literature of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Electric Literature of C15H12N2S

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

Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines was written by McLean, Liam A.;Ashford, Matthew W.;Fyfe, James W. B.;Slawin, Alexandra M. Z.;Leach, Andrew G.;Watson, Allan J. B.. And the article was included in Chemistry – A European Journal in 2022.Category: thiazole This article mentions the following:

A method for the synthesis of chiral vicinal chloroamines RCH(Cl)CH₂NHR¹ [R = 2-quinolyl, quinazolin-2-yl, 1,3-benzothiazol-2-yl, etc.; R¹ = Ph, 4-MeC₆H₄, benzothiophen-5-yl, etc.] via asym. protonation of catalytically generated prochiral chloroenamines using chiral Bronsted acids was reported. The process was highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations The utility of the method showed as an approach to the synthesis of a broad range of heterocycle-substituted aziridines I [R² = 2-quinolyl, quinoxalin-2-yl, 5-cyano-2-pyridyl, etc.; Ar = Ph, 4-MeOC₆H₄, 3-BrC₆H₄, etc.] by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines II [R³ = 4-tert-butoxycarbonylpiperazin-1-yl, morpholino, thiomorpholino]. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) 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. 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

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C-H sulfurization: a new route to 2-aminobenzothiazoles was written by Yao, Guangkai;Wang, Bing-Feng;Yang, Shuai;Zhang, Zhi-Xiang;Xu, Han-Hong;Tang, Ri-Yuan. And the article was included in RSC Advances in 2019.Synthetic Route of C13H10N2S This article mentions the following:

DMSO was found to activate arylisothiocyanates for self-nucleophilic addition A subsequent intramol. C-H sulfurization catalyzed by PdBr₂ enable accessed to a wide range of 2-aminobenzothiazole derivatives in moderate to good yields. This is the first example of a DMSO-mediated Pd-catalyzed synthesis of 2-aminobenzothiazoles through cyclization/C-H sulfurization of two isothiocyanates. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).

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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Synthetic Route of C13H10N2S

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

Benzothiazole. I. Nitration and bromination of 2-chlorobenzothiazole was written by Colonna, Martino. And the article was included in Pubbl. ist. chim. univ. Bologna in 1943.HPLC of Formula: 80945-86-4 This article mentions the following:

According to the hypothesis of Bonino (C.A. 34, 323.6) direct “cationoid” substitution (halogenation, nitration, etc.) of benzothiazole (I) should be directed toward the positions of the H atoms statistically pos., i. e., 4 or 6, while “anionoid” substitution (e. g., with NaNH₂, NH₂OH, etc.) should be directed toward the positions of the H atom statistically neg., i. e., 2. In order to test these predictions, 2-chlorobenzothiazole (II) was prepared (cf. Ger. pat. 516,996 (C.A. 25, 3015)) by the action of PCl₅ and POCl₃ on 2-mercaptobenzothiazole (III). II dissolved in concentrated H₂SO₄, treated with EtNO₃ at 0°, gives a crystalline precipitate of 2-chloro-6-nitrobenzothiazole (IV), m. 192°, which at 140° (under pressure) with alc. NH₃ gives 2-amino-6-nitrobenzothiazole (V), yellow, m. 245° (alc.), identical with the compound obtained by treating p-nitro-aniline with NH₄CNS (cf. Kauffmann, C.A. 29, 2660.1). IV with Br in CHCl₃ gives 2-chloro-6-bromobenzothiazole, white, m. 100-1°, and the same compound is obtained by treating the diazo derivative of IV with Cu₂Br₂. The structure of I according to Bonino shows the pyridine-like character of the N atom, and the strictly aromatic character of the benzene nucleus; however, in this nucleus the tricentered bond is fixed, while in other nuclei it is of an oscillating type, as in the equilibrium of quinoline: (VI)⇌ (VII). In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4HPLC of Formula: 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.HPLC of Formula: 80945-86-4

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

Design, synthesis, and biologic evaluation of novel galloyl derivatives as HIV-1 RNase H inhibitors was written by Gao, Ping;Wang, Xueshun;Sun, Lin;Cheng, Xiqiang;Poongavanam, Vasanthanathan;Kongsted, Jacob;Alvarez, Mar;Luczkowiak, Joanna;Pannecouque, Christophe;De Clercq, Erik;Lee, Kuo-Hsiung;Chen, Chin-Ho;Liu, Huiqing;Menendez-Arias, Luis;Liu, Xinyong;Zhan, Peng. And the article was included in Chemical Biology & Drug Design in 2019.Recommanded Product: 69812-29-9 This article mentions the following:

Human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H (RNase H) remains as the only enzyme encoded within the viral genome not targeted by current antiviral drugs. In this work, we report the design, synthesis, and biol. evaluation of a novel series of galloyl derivatives with HIV-1 RNase H inhibitory activity. Most of them showed IC₅₀s at sub- to low-micromolar concentrations in enzymic assays. The most potent compound was II-25 that showed an IC₅₀ of 0.72 ± 0.07 μM in RNase H inhibition assays carried out with the HIV-1_BH10 RT. II-25 was 2.8 times more potent than β-thujaplicinol in these assays. Interestingly, II-25 and other galloyl derivatives were also found to inhibit the HIV IN strand transfer activity in vitro. Structure-activity relationships (SAR) studies and mol. modeling anal. predict key interactions with RT residues His539 and Arg557, while providing helpful insight for further optimization of selected compounds In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Recommanded Product: 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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 δ 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.Recommanded Product: 69812-29-9

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

Novel and Efficient Synthesis of Benzimidazole and Benzthiazole Moieties Mediated by Triflic Anhydride and 2-Nitropyridine was written by Quadri, Syed Aziz Imam;Das, Tonmoy C.;Farooqui, Mazahar. And the article was included in ChemistrySelect in 2017.Computed Properties of C7H4ClNOS This article mentions the following:

In the present report, inter and intramol. C-N bond formation between the carbonyl carbon of urea or amide functional group with various amines, e.g., I, mediated by triflic anhydride and 2-nitropyridine is successfully investigated for the first time. The versatility of the method is demonstrated by exploring it on a wide range of substrates to synthesize diversified 2-aminobenzimidazoles II [Y = NH; R = H; R¹ = 4-ClC₆H₄NH, 1H-pyrazol-1-yl, 1H-indazol-1-yl, etc.], 2-aminobenzothiazoles II [Y = S; R = H, Cl; R¹ 2-O₂N-4-F₃CC₆H₃NH, 4-CN-3-F₃CC₆H₃, [6-cyano-5-(trifluoromethyl)pyridin-3-yl]aminyl, etc.], 2-aminopyridoimidazoles III [R³ = H, Cl; X = N; Z = NH₂; R² = C₂H₅, (CH₃)₂CHCH₂] and 2-substituted benzimidazoles III [X = CH; R = H; R² = Me, Et, Pr, (CH₃)₃CCH₂; Z = Cy, furan-2-yl, 4-BrC₆H₄, etc.]. Short reaction time, high yields and applicability in milder metal free reaction conditions are the highlights of the present methodol. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Computed Properties of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. 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.Computed Properties of C7H4ClNOS

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