Category: thiazole

Use of a Pharmacophore Model To Discover a New Class of Influenza Endonuclease Inhibitors was written by Parkes, Kevin E. B.;Ermert, Philipp;Faessler, Juerg;Ives, Jane;Martin, Joseph A.;Merrett, John H.;Obrecht, Daniel;Williams, Glyn;Klumpp, Klaus. And the article was included in Journal of Medicinal Chemistry in 2003.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Data from both our own and literature studies of the biochem. and inhibition of influenza virus endonuclease was combined with data on the mechanism of action and the likely active site mechanism to propose a pharmacophore. The pharmacophore was used to design a novel structural class of inhibitors, some of which were found to have activities similar to that of known influenza endonuclease inhibitors and were also antiviral in cell culture. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Sequencing [4+1]-Cycloaddition and Aza-Michael Addition Reactions: A Diastereoselective Cascade for the Rapid Access of Pyrido[2′,1′:2,3]/Thiazolo[2′,3′:2,3]imidazo[1,5-a]quinolone Scaffolds as Potential Antibacterial and Anticancer Motifs was written by Srinivasulu, Vunnam;Khanfar, Monther;Omar, Hany A.;ElAwady, Raafat;Sieburth, Scott McN;Sebastian, Anusha;Zaher, Dana M.;Al-Marzooq, Farah;Hersi, Fatema;Al-Tel, Taleb H.. And the article was included in Journal of Organic Chemistry in 2019.Category: thiazole This article mentions the following:

The design and synthesis of a quality compound library containing a small number of skeletally diverse scaffolds, whose members rapidly deliver new chem. probes active against multiple phenotypes, is paramount in drug discovery. In this context, an efficient one-pot strategy for the synthesis of a mini library of sp3 enriched hexahydropyrido[2′,1′:2,3]imidazo[1,5-a]quinolinium and hexahydrothiazolo[2′,3′:2,3] imidazo[1,5-a]quinolinium architectures, is described. This new one-pot method features a combination of Sc(OTf)3-catalyzed [4+1]-cycloaddition with aza-Michael addition reactions.The cascade results in a rapid and diastereoselective formation of these scaffolds via desymmetrization of the oxidative-dearomatization products of phenols. Phenotypic screening of the mini library against multidrug resistant bacteria and a panel of cancer cell lines identified potential antibacterial and anticancer lead drug candidates.Further investigation of the anticancer leads, indicated their activity as tubulin-polymerization inhibitors, representing a promising approach for cancer therapy. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Category: thiazole).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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.Category: thiazole

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

Ligand free copper-catalyzed N-arylation of heteroarylamines was written by Wang, Deping;Kuang, Daizhi;Zhang, Fuxing;Liu, Yang;Ning, Shunhua. And the article was included in Tetrahedron Letters in 2014.Recommanded Product: 1843-21-6 This article mentions the following:

An efficient protocol for the ligand-free Cu-catalyzed N-arylation of heteroarylamines was developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines affording the corresponding products in high yields. Furthermore, this protocol was particularly suitable for reactions of hindered aryl iodides with 2-aminopyridines. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 1843-21-6

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

Photoredox-Mediated C-H Functionalization and Coupling of Tertiary Aliphatic Amines with 2-Chloroazoles was written by Singh, Anuradha;Arora, Amandeep;Weaver, Jimmie D.. And the article was included in Organic Letters in 2013.Synthetic Route of C9H6ClNS This article mentions the following:

Herein, conditions for C-H functionalization of tertiary aliphatic amines and their subsequent coupling with a number of 2-chloroazole derivatives are reported. The reaction is facilitated by a catalytic amount of tris-fac-Ir(ppy)₃, with blue light irradiation and takes place under mild and convenient conditions. Most couplings take place with excellent regioselectivity. The reaction is tolerant of a number of functional groups and allows for rapid access to α-azole carbinamines e. g., I and II commonly found in post-translationally modified peptides. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Synthetic Route of C9H6ClNS).

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

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

A Practical Copper Catalyzed N-Arylation of Amines Using Aryl Triazenes as Aryl Source was written by Chand, Shiv;Kumar, Saurabh;Singh, Rahul;Singh, Krishna Nand. And the article was included in ChemistrySelect in 2019.Application of 1843-21-6 This article mentions the following:

An efficient copper-catalyzed synthesis of N-arylated amines was developed via cross-coupling of amines with aryl triazenes. The methodol. was endowed with broad substrate scope, high yield and significant functional group tolerance. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

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

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

Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C-N and C-O coupling reactions was written by Majumder, Arpi;Gupta, Ragini;Mandal, Mrinmay;Babu, Madhu;Chakraborty, Debashis. And the article was included in Journal of Organometallic Chemistry in 2015.Reference of 1843-21-6 This article mentions the following:

This paper describes an efficient procedure for palladium(0)-catalyzed N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulfide ligands and their corresponding Pd(0) complexes namely [Pd(p₂S₂)(dba)] and [Pd(pp₃S₄)(dba)], were synthesized, where p₂S₂ is 1,2-bis(diphenylphosphino)ethane disulfide, pp₃S₄ is tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide, and dba is dibenzylideneacetone. Optimal reaction conditions were determined for the arylation reactions using iodobenzene and benzimidazole by varying temperature, solvent, base, and catalyst loading. The cross coupling reactions were carried out taking iodobenzenes/bromobenzenes and a wide variety of substituted aryl amines/phenols/alcs. with different steric and electronic properties to afford the desired N-arylamines/diaryl ethers/alkyl aryl ethers in good to excellent yield (70-94%). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Reference of 1843-21-6

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

Synthesis, biological evaluation and in silico modeling of novel integrase strand transfer inhibitors (INSTIs) was written by Ivashchenko, Andrey A.;Ivanenkov, Yan A.;Koryakova, Angela G.;Karapetian, Ruben N.;Mitkin, Oleg D.;Aladinskiy, Vladimir A.;Kravchenko, Dmitry V.;Savchuk, Nikolai P.;Ivashchenko, Alexander V.. And the article was included in European Journal of Medicinal Chemistry in 2020.Application In Synthesis of Thiazol-2-ylmethanamine This article mentions the following:

Although a relatively wide range of therapeutic options is currently available for the treatment of HIV/AIDS, it is still among the most serious and virulent diseases and is associated with a high mortality rate. Integrase strand transfer inhibitors (INSTIs), e.g., FDA-approved dolutegravir (DTG), bictegravir (BIC) and cabotegravir (CAB), have recently been included in standard highly active antiretroviral therapy (HAART) schemes as one of the five major components responsible for the most beneficial clin. outcome. In this paper, we describe a combinatorial amide synthesis, biol. evaluation and in silico modeling of new INSTIs containing heteroaromatic bioisosteric substitution instead of the well-studied halogen-substituted benzyl fragment. With the focus on the mentioned diversity point, a medium-sized library of compounds was selected for synthesis. A biol. study revealed that many mols. were highly active INSTIs (EC₅₀ < 10 nM). Two compounds 1{4} and 1{26} demonstrated picomolar antiviral activity that was comparable with CAB and were more active than DTG and BIC. Mol. docking study was performed to evaluate the binding mode of compounds in the active site of HIV-1 IN. In rats, lead compound 1{26} showed two-fold greater bioavailability than CAB and had a similar half-life. Compound 1{26} and its sodium salt were considerably more soluble in water than the parent drugs. Both mols. were very stable in human liver microsomes and plasma, demonstrated high affinity towards plasma proteins and did not show cytochrome (CYP) inhibition. This benefit profile indicates the great potential of these mols. as attractive candidates for subsequent evaluation as oral long-acting drugs and long-acting nanosuspension formulations for i.m. injection. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Application In Synthesis of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Application In Synthesis of Thiazol-2-ylmethanamine

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

Synthesis and Biological Activity of Sulfonamide Derivatives of Epipodophyllotoxin was written by Guianvarc’h, Dominique;Duca, Maria;Boukarim, Chawki;Kraus-Berthier, Laurence;Leonce, Stephane;Pierre, Alain;Pfeiffer, Bruno;Renard, Pierre;Arimondo, Paola B.;Monneret, Claude;Dauzonne, Daniel. And the article was included in Journal of Medicinal Chemistry in 2004.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

A series of novel 4β-substituted sulfonamide derivatives of 4′-O-demethyl-4-desoxypodophyllotoxin, I [R¹ = SO₂R, R = Me, n-Pr, (CH₂)₃NH₂, 2-thienyl, piperidino, etc.] (II), has been synthesized. II were synthesized by silylating the alc. I (R¹ = H), followed by reaction with RSO₂Cl, and desilylation. Their effects on human DNA topoisomerase II and, in some cases, on tubulin polymerization were evaluated. Several of the compounds, e.g. II (R = Me), and the synthetic precursor, the 4β-azido compound, are potent topoisomerase II poisons that induce double-stranded breaks in DNA, with either improved or similar activity compared to etoposide. Only the amino precursor, compound I (R¹ = H), was slightly active in tubulin polymerization inhibition assays. We observed that the derivatives bearing an aromatic ring on the 4β-sulfonamide substituent were either less cytotoxic or equivalent to the parent drug, while the sulfonamides containing an aliphatic side chain and the amino-sulfonamide derivatives, except II [R = (CH₂)₁₅Me, (CH₂)₃NH₂], exhibited increased cytotoxicity compared to etoposide. In vivo, against the P388 leukemia and the A-549 orthotopic model of lung carcinoma, the most promising compounds were the morpholino- and the piperazino-containing sulfonamides derivatives II (R = morpholino, 4-methylpiperazino). In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Electric Literature of C6H7ClN2O3S2

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

Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions was written by Zhou, Bohao;Hong, Hailong;Wang, Hongcai;Zhang, Tianmiao;Han, Limin;Zhu, Ning. And the article was included in European Journal of Organic Chemistry in 2018.Electric Literature of C7H4ClNOS This article mentions the following:

Carbonyl sulfide (COS), whose mol. structure is similar to CO₂ and CS₂, could be used as a better alternative carbonyl reagent due to its high chem. activity. However, the unfriendly byproduct H₂S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H₂S generation and S-S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S-S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodol. provided a promising process for the utilization of COS. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Electric Literature of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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.Electric Literature of C7H4ClNOS

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

Development and evaluation of selective, reversible LSD1 inhibitors derived from fragments was written by Hitchin, James R.;Blagg, Julian;Burke, Rosemary;Burns, Samantha;Cockerill, Mark J.;Fairweather, Emma E.;Hutton, Colin;Jordan, Allan M.;McAndrew, Craig;Mirza, Amin;Mould, Daniel;Thomson, Graeme J.;Waddell, Ian;Ogilvie, Donald J.. And the article was included in MedChemComm in 2013.Safety of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Two series of aminothiazoles have been developed as reversible inhibitors of lysine specific demethylase 1 (LSD1) through the expansion of a hit derived from a high concentration biochem. fragment based screen of 2466 compounds The potency of the initial fragment hit was increased 32-fold through synthesis, with one series of compounds showing clear structure-activity relationships and inhibitory activities in the range of 7 to 187 μM in a biochem. assay. This series also showed selectivity against the related FAD-dependent enzyme mono-amine oxidase A (MAO-A). Although a wide range of irreversible inhibitors of LSD1 have been reported with activities in the low nanomolar range, this work represents one of the first reported examples of a reversible small mol. inhibitor of LSD1 with clear SAR and selectivity against MAO-A, and could provide a platform for the development of more potent reversible inhibitors. Herein, we also report the use of a recently developed cell-based assay for profiling LSD1 inhibitors, and present results on our own compounds as well as a selection of recently described reversible LSD1 inhibitors. 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 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Safety of 4,5-Diphenylthiazol-2-amine

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