Day: January 5, 2023

Discovery of a quorum sensing modulator pharmacophore by 3D small-molecule microarray screening was written by Marsden, David M.;Nicholson, Rebecca L.;Skindersoe, Mette E.;Galloway, Warren R. J. D.;Sore, Hannah F.;Givskov, Michael;Salmond, George P. C.;Ladlow, Mark;Welch, Martin;Spring, David R.. And the article was included in Organic & Biomolecular Chemistry in 2010.Safety of Thiazol-2-ylmethanamine This article mentions the following:

The screening of large arrays of drug-like small-mols. was traditionally a time consuming and resource intensive task. New methodol. developed within the authors’ laboratories provides an attractive low cost, 3D microarray-assisted screening platform that could be used to rapidly assay thousands of compounds As a proof-of-principle the platform was exploited to screen a number of quorum sensing analogs. Quorum sensing was used by bacterium to initiate and spread infection; in this context its modulation may have significant clin. value. 3D microarray slides were probed with fluorescently labeled ligand-binding domains of the LuxR homolog CarR from Erwinia carotovora subsp. carotovora. The 3D microarray platform was used to discover the biol. active chloro-pyridine pharmacophore, which was validated using a fluorometric ligand binding assay and ITC. Analogs containing the chloro-pyridine pharmacophore are potent inhibitors of N-acyl-homoserine-lactone (AHL) mediated quorum sensing phenotypes in Serratia (IC₅₀ ≃5 μM) and Pseudomonas aeruginosa (IC₅₀ = 10-20 μM). 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. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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

Factor Xa Inhibitors: S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides was written by Chan, Chuen;Borthwick, Alan D.;Brown, David;Burns-Kurtis, Cynthia L.;Campbell, Matthew;Chaudry, Laiq;Chung, Chun-wa;Convery, Maire A.;Hamblin, J. Nicole;Johnstone, Lisa;Kelly, Henry A.;Kleanthous, Savvas;Patikis, Angela;Patel, Champa;Pateman, Anthony J.;Senger, Stefan;Shah, Gita P.;Toomey, John R.;Watson, Nigel S.;Weston, Helen E.;Whitworth, Caroline;Young, Robert J.;Zhou, Ping. And the article was included in Journal of Medicinal Chemistry in 2007.Name: 6-Chlorobenzo[d]thiazol-2(3H)-one This article mentions the following:

Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and mol. modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified (I) as a candidate for further evaluation. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Name: 6-Chlorobenzo[d]thiazol-2(3H)-one).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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.Name: 6-Chlorobenzo[d]thiazol-2(3H)-one

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

Quaternization at an Sp² nitrogen. II. An analysis on the substituent effect and on the nature of the transition state was written by Behera, G. B.;Sharma, A.. And the article was included in Bulletin of the Chemical Society of Japan in 1979.Computed Properties of C15H12N2S This article mentions the following:

The kinetics of N-phenacylation of a number of substituted thiazoles with substituted phenacyl bromides were investigated in PhNO₂ and in a number of other dipolar aprotic solvents. The rate constants of 2-amino-4-phenylthiazoles and 2-aminobenzothiazoles were calculated with suitably developed equations. The deviation of the observed values from the calculated results was ascribed to the steric effect. A 7-membered H-bonded transition state was proposed on the basis of the results obtained from the substituent and medium effects. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Computed Properties of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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 C15H12N2S

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

Renal functional changes in experimental cystic disease are tubular in origin. was written by Carone, F A;Ozono, S;Samma, S;Kanwar, Y S;Oyasu, R. And the article was included in Kidney international in 1988.Safety of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Chronic (30 weeks) structural and functional changes were correlated in diphenylthiazole (DPT)-induced polycystic kidney disease (PKD) in rats. DPT induced two different types of progressive tubular changes: cystic transformation and hyperplastic/atrophic tubular changes. Cystic changes diffusely involved collecting tubules in the outer medulla and cortex, and they were progressive over 30 weeks. Hyperplastic/atrophic changes occurred as clusters of tubules in the cortex and involved between 25% and 50% of tubular profiles after 12 and 30 weeks of drug treatment. Thus, the two types of tubular change were independent of each other and represent different cellular responses to the drug. DPT treatment induced no detectable light- and electron-microscopic or histochemical alterations in glomeruli or renal blood vessels. Renal functional changes consisted of: (1) early (4 weeks) and persistent impairment of concentrating ability; (2) a progressive drop in creatinine clearance and elevation in BUN; and (3) the late onset (30 weeks) of moderate proteinuria. These findings suggest that cystic as well as hyperplastic-atrophic tubular changes contribute to the loss of tubular and renal function in DPT-induced PKD. Both types of tubular lesions may have a role in the development of impaired renal function in other forms of experimental and clinical PKD. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Safety of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Safety of 4,5-Diphenylthiazol-2-amine

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

Decreased de novo synthesis of proteoglycans in drug-induced renal cystic disease was written by Lelongt, Brigitte;Carone, Frank A.;Kanwar, Yashpal S.. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 1988.HPLC of Formula: 6318-74-7 This article mentions the following:

Cellular and extracellular (tubular basement membrane, TBM) alterations in the proteoglycans (PGs) of the rat renal tubules in diphenylthiazole-induced cystic disease were investigated. The PGs of normal and cystic kidneys were labeled with [³⁵S]sulfate in an organ-perfusion system. Extracted cellular and TBM PGs were characterized by Sepharose CL-6B chromatog. before or after treatment with heparitinase (degrades heparan sulfate) or chondroitinase ABC (degrades chondroitin sulfate). Total radioactivities in cellular, TBM, and medium fractions of cystic kidneys were reduced by factors of 9, 7, and 3, resp. The PGs obtained from cystic and normal kidneys had similar profiles, namely, two peaks of radioactivity with K_av values of 0.26 (M_r = 130,000-150,000) and 0.40 (M_r = 50,000-55,000). The peaks had variable proportions of radioactivity for cellular and TBM fractions. Besides heparan sulfate, an addnl. 15-20% of chondroitin sulfate was synthesized in all three fractions obtained from cystic kidneys. The PGs synthesized by cystic kidneys had lower charge-d. characteristics as compared to controls by DEAE-Sepharose chromatog. The medium fractions contained mostly glycosaminoglycan chains of heparan sulfate. Autoradiograms of tissue samples revealed ≈50% and ≈60% decreases of grain densities over the cellular and TBM compartments, resp. This decrease in de novo PG synthesis may have some relationship in the pathogenesis of polycystic kidney disease. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7HPLC of Formula: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.HPLC of Formula: 6318-74-7

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

Base and ligand free copper-catalyzed N-arylation of 2-amino-N-heterocycles with boronic acids in air was written by Rao, D. Nageswar;Rasheed, Sk.;Aravinda, S.;Vishwakarma, Ram A.;Das, Parthasarathi. And the article was included in RSC Advances in 2013.SDS of cas: 1843-21-6 This article mentions the following:

A wide range of N-arylated 2-amino-N-heterocycles were synthesized by a copper-catalyzed boronic acid cross coupling reaction at ambient temperature in air. This ligand and base free methodol. is general and could provide rapid access to a diverse array of potential bioactive heterocyclic compounds In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 1843-21-6).

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

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

Synthesis and evaluation of amides surrogates of dopamine D3 receptor ligands was written by Jean, Mickael;Renault, Jacques;Levoin, Nicolas;Danvy, Denis;Calmels, Thierry;Berrebi-Bertrand, Isabelle;Robert, Philippe;Schwartz, J. C.;Lecomte, J. M.;Uriac, Philippe;Capet, Marc. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H6ClNS This article mentions the following:

Isosteric replacement of the amide function and modulation of the arylpiperazine moiety of known dopamine D3 receptor ligands led to potent and selective compounds Enhanced bioavailability and preferential brain distribution make (piperazinyl)butanamine derivative I a good candidate for pharmacol. and clin. evaluation. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Formula: C9H6ClNS).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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. 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: C9H6ClNS

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

Photocatalytic intermolecular carboarylation of alkenes by selective C-O bond cleavage of diarylethers was written by Ji, Meishan;Chang, Chenyang;Wu, Xinxin;Zhu, Chen. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.COA of Formula: C7H3BrClNS This article mentions the following:

Disclosed herein is a novel radical-mediated intermol. carboarylation of alkenes by cleaving inert C-O bonds. The strategically designed arylbenzothiazolylether diazonium salts are harnessed as dual-function reagents. A vast array of alkenes are proven to be suitable substrates. The benzothiazolyl moiety in the products serves as the formyl precursor, and the OH residue provides the cross-coupling site for further product elaboration, indicating the robust transformability of the products. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4COA of Formula: C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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 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.COA of Formula: C7H3BrClNS

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

Metal-free synthesis of 2-substituted (N, O, C) benzothiazoles via an intramolecular C-S bond formation was written by Feng, Enguang;Huang, He;Zhou, Yu;Ye, Deju;Jiang, Hualiang;Liu, Hong. And the article was included in Journal of Combinatorial Chemistry in 2010.Formula: C13H10N2S This article mentions the following:

An efficient, economical, and convenient method was developed for the preparation of 2-substituted (N, O, C) benzothiazoles from N’-substituted-N-(2-halophenyl)thioureas, O’-substituted-N-(2-halophenyl) carbamothioates, or N-(2-halophenyl) thioamides via a base-promoted cyclization in dioxane without any transition metal. A one-pot variant combining the synthesis of the thiourea and the cyclization was also demonstrated. High yields were obtained, and a variety of functional groups were tolerated under these conditions. Transition-metal-free, mild reactive conditions, wide application scope, and shorter reaction times make this method superior to the reported methods for the synthesis of 2-substituted benzothiazoles and suitable for combinatorial format. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: 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). 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.Formula: C13H10N2S

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

Novel triapine derivative induces copper-dependent cell death in hematopoietic cancers was written by Chen, Ge;Niu, Chunyi;Yi, Jianhua;Sun, Lin;Cao, Hengyi;Fang, Yanjia;Jin, Taijie;Li, Ying;Lou, Chunli;Kang, Jingwu;Wei, Wanguo;Zhu, Jidong. And the article was included in Journal of Medicinal Chemistry in 2019.Category: thiazole This article mentions the following:

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clin. trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematol. malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10(I)) with potent antitumor activity. I preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, I executed cytotoxic action in a copper-dependent manner. I-induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, I showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies I as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Category: thiazole).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Category: thiazole

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