Tag: 100-200

Importance of substituents in ring opening: a DFT study on a model reaction of thiazole to thioamide was written by Bai, Xue;Qin, Dan;Yang, Lijun. And the article was included in Journal of Molecular Modeling in 2021.Recommanded Product: 2-Methylthiazol-5-amine This article mentions the following:

Thiazole ring is an important active mol. skeleton of drugs. Thiazole in natural products and drugs are usually harmlessly eliminated. However, hepatotoxic reactions may occur due to the biol. activation of thiazole to produce reactive thioamide. A typical example is hepatotoxic sudoxicam and safety meloxicam. The only structural difference between them is a Me group on C5 position of thiazole in meloxicam. The mol. basis for the difference remains unknown and the bioactivation mechanism of the thiazole ring is still obscure. Quantum chem. calculations were performed to elucidate the activation mechanism of the thiazole ring under P 450 catalysis, and the influence of the substituents on the activation pathways of thiazole ring was also studied. The calculated results show that the activation of thiazole is closely related to the substituents on the thiazole and spin state of Cpd I. The thiazole and substituted thiazole directly open the ring when catalyzed by doublet spin state Cpd I that catalyzed by the quartet spin state Cpd I can open the ring directly or indirectly, which is related to the substituents. Thiazoles modified with electron-donating substituents mainly undergo direct ring opening, while thiazoles modified with electron-withdrawing groups or weak electron-donating groups mainly undergo indirect ring-opening process accompanied by intermediate formation. The research results laid the foundation for the design of thiazole ring drugs, and also laid a theor. foundation for the study of reducing the toxicity of thiazole ring drugs. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Recommanded Product: 2-Methylthiazol-5-amine).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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: 2-Methylthiazol-5-amine

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

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

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

Oxidation potentials and ionization potentials of some phenyl derivatives of thiazole was written by Bonnier, Jane Marie;Arnaud, Roger;Maurey-Mey, Monique. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1968.HPLC of Formula: 1826-13-7 This article mentions the following:

The half-wave oxidation potentials and the ionization potentials (determined from the charge transfer of the complexes and by the Hueckel method) are given for thiazole, 2-, 4-, and 5-phenylthiazole, 2,4-, 2,5-, and 4,5-diphenylthiazole, 2-phenyl-4-biphenylylthiazole, 4-phenyl-2-biphenylylthiazole, and 2,4-bis(biphenylyl)thiazole. A linear relation existed between the ionization potentials and the halfwave oxidation potentials. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7HPLC of Formula: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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.HPLC of Formula: 1826-13-7

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

Lewis Acid-Catalyzed, Copper(II)-Mediated Synthesis of Heteroaryl Thioethers under Base-Free Conditions was written by Dai, Chao;Xu, Zhaoqing;Huang, Fei;Yu, Zhengkun;Gao, Yan-Feng. And the article was included in Journal of Organic Chemistry in 2012.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

A Lewis acid (Ag^I, Ni^II, or Fe^II) catalyzed, Cu^II-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic Me thioethers. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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.Application In Synthesis of 5-Phenylthiazole

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

Discovery of Novel Small Molecules that Activate Satellite Cell Proliferation and Enhance Repair of Damaged Muscle was written by Billin, Andrew N.;Bantscheff, Marcus;Drewes, Gerard;Ghidelli-Disse, Sonja;Holt, Jason A.;Kramer, Henning F.;McDougal, Alan J.;Smalley, Terry L.;Wells, Carrow W.;Zuercher, William J.;Henke, Brad R.. And the article was included in ACS Chemical Biology in 2016.Safety of Thiazol-2-ylmethanamine This article mentions the following:

Skeletal muscle progenitor stem cells (referred to as satellite cells) represent the primary pool of stem cells in adult skeletal muscle responsible for the generation of new skeletal muscle in response to injury. Satellite cells derived from aged muscle display a significant reduction in regenerative capacity to form functional muscle. This decrease in functional recovery has been attributed to a decrease in proliferative capacity of satellite cells. Hence, agents that enhance the proliferative abilities of satellite cells may hold promise as therapies for a variety of pathol. settings, including repair of injured muscle and age- or disease-associated muscle wasting. Through phenotypic screening of isolated murine satellite cells, we identified a series of 2,4-diaminopyrimidines (e.g., 2) that increased satellite cell proliferation. Importantly, compound 2 was effective in accelerating repair of damaged skeletal muscle in an in vivo mouse model of skeletal muscle injury. While these compounds were originally prepared as c-Jun N-terminal kinase 1 (JNK-1) inhibitors, structure-activity analyses indicated JNK-1 inhibition does not correlate with satellite cell activity. Screening against a broad panel of kinases did not result in identification of an obvious mol. target, so we conducted cell-based proteomics experiments in an attempt to identify the mol. target(s) responsible for the potentiation of the satellite cell proliferation. These data provide the foundation for future efforts to design improved small mols. as potential therapeutics for muscle repair and regeneration. 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. 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.Safety of Thiazol-2-ylmethanamine

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

Synthesis and bio-activity evaluation of tetraphenyl(phenylamino) methylene bisphosphonates as antioxidant agents and as potent inhibitors of osteoclasts in vitro was written by Balakrishna, A.;Reddy, M. Veera Narayana;Rao, P. Visweswara;Kumar, M. Anil;Kumar, B. Siva;Nayak, S. K.;Reddy, C. Suresh. And the article was included in European Journal of Medicinal Chemistry in 2011.Quality Control of 2-Methylthiazol-5-amine This article mentions the following:

A new series of tetra-Ph bisphosphonates have been elegantly synthesized by one-pot method and were characterized by elemental anal., FTIR, ¹H, ¹³C, ³¹P NMR, mass spectra and evaluated for their in vitro anti-bone resorptive activity by inhibiting growth of osteoclasts. Two bisphosphonates showed marked inhibition ratio (8 μM and 10 μM) and emerged as lead compounds All compounds were tested for their antioxidant (DPPH scavenging, reducing power and inhibition of lipid peroxidation). They exhibited potent in vitro antioxidant activity dose-dependently. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Quality Control of 2-Methylthiazol-5-amine).

2-Methylthiazol-5-amine (cas: 89281-44-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Quality Control of 2-Methylthiazol-5-amine

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

Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase was written by Balti, Monaem;Plas, Aurelie;Meinguet, Celine;Haufroid, Marie;Themans, Quentin;Efrit, Mohamed Lotfi;Wouters, Johan;Lanners, Steve. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Quality Control of 2-Chloro-5-phenylthiazole This article mentions the following:

Docking studies of 4-phenylthiazolinethione on human IDO1 suggest complexation of the heme iron by the exocyclic sulfur atom further reinforced by hydrophobic interactions of the Ph ring within pocket A of the enzyme. On this basis, chem. modifications were proposed to increase inhibitory activity. Synthetic routes had to be adapted and optimized to yield the desired substituted 4- and 5-arylthiazolinethiones I (X = 2-OCH₃, 3-F, 4-CN, etc.) and II (X = H, 2-OCH₃, 3-Br, etc.). Their biol. evaluation shows that 5-aryl regioisomers are systematically less potent than the corresponding 4-aryl analogs. Substitution on the Ph ring does not significantly increase inhibition potency, except for 4-Br and 4-Cl derivatives In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Quality Control of 2-Chloro-5-phenylthiazole).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Quality Control of 2-Chloro-5-phenylthiazole

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

Programmed synthesis of arylthiazoles through sequential C-H couplings was written by Tani, Satoshi;Uehara, Takahiro N.;Yamaguchi, Junichiro;Itami, Kenichiro. And the article was included in Chemical Science in 2014.Computed Properties of C9H7NS This article mentions the following:

A programmed synthesis of arylthiazoles (2-aryl, 4-aryl, 5-aryl, 2,4-diaryl, 2,5-diaryl, 4,5-diaryl, and 2,4,5-triaryl) via palladium or nickel catalyzed sequential C-H couplings of unfunctionalized thiazole using eleven distinct synthetic routes was discussed. This methodol. led to the synthesis of over 150 arylthiazoles including fatostatin (SREBP inhibitor). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.Computed Properties of C9H7NS

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