Category: thiazole

Artificial hibernation/life-protective state induced by thiazoline-related innate fear odors was written by Matsuo, Tomohiko;Isosaka, Tomoko;Tang, Lijun;Soga, Tomoyoshi;Kobayakawa, Reiko;Kobayakawa, Ko. And the article was included in Communications Biology in 2021.Computed Properties of C4H7NS This article mentions the following:

Innate fear intimately connects to the life preservation in crises, although this relationships is not fully understood. Here, we report that presentation of a supernormal innate fear inducer 2-methyl-2-thiazoline (2MT), but not learned fear stimuli, induced robust systemic hypothermia/hypometabolism and suppressed aerobic metabolism via phosphorylation of pyruvate dehydrogenase, thereby enabling long-term survival in a lethal hypoxic environment. These responses exerted potent therapeutic effects in cutaneous and cerebral ischemia/reperfusion injury models. In contrast to hibernation, 2MT stimulation accelerated glucose uptake in the brain and suppressed oxygen saturation in the blood. Whole-brain mapping and chemogenetic activation revealed that the sensory representation of 2MT orchestrates physiol. responses via brain stem Sp5/NST to midbrain PBN pathway. 2MT, as a supernormal stimulus of innate fear, induced exaggerated, latent life-protective effects in mice. If this system is preserved in humans, it may be utilized to give rise to a new field: “sensory medicine”. In the experiment, the researchers used many compounds, for example, 2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1Computed Properties of C4H7NS).

2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Computed Properties of C4H7NS

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

Electroorganic preparations. XVI. Polarography and reduction of quinazoline was written by Lund, Henning. And the article was included in Acta Chemica Scandinavica in 1965.Synthetic Route of C4H5BrN2S This article mentions the following:

The polarographic reduction of quinazoline (I) was observed throughout the pH range 0-12 and in more acid media (acidity function H₊ to -2); 2 waves were observed. For the 1st wave the limiting current is diffusion controlled at pH 5 but is kinetically controlled at pH 1. The abnormal pH dependence of the limiting current can be explained by hydration of the protonated I nucleus if it is assumed that only the normal cation and not the hydrated cation is polarographically reducible. The rate constant of the dehydration was determined from polarographic data, and the dehydration was found to be specific acid catalyzed. The second wave of I is a reduction of the 3,4-dihydroquinazoline (II) formed in the first reduction at low concentrations of I. II was reduced in borate buffer to 1,2,3,4-tetrahydroquinazoline. I yields on controlled potential reduction both in acid and alk. solution a dimerized product, which probably is dimerized at C-4. The product can be reoxidized to I with hexacyanoferrate(III) in alk. solution In the experiment, the researchers used many compounds, for example, 2-Amino-5-bromo-4-methylthiazole (cas: 3034-57-9Synthetic Route of C4H5BrN2S).

2-Amino-5-bromo-4-methylthiazole (cas: 3034-57-9) 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.Synthetic Route of C4H5BrN2S

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

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation was written by Mao, Shuai;Zhao, Yahao;Luo, Zixuan;Wang, Ruizhe;Yuan, Bo;Hu, Jianping;Hu, Linghao;Zhang, San-Qi;Ye, Xiaoxing;Wang, Mingliang;Chen, Zhengkai. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2022.Synthetic Route of C7H9NS This article mentions the following:

A photo-induced C-S radical cross-coupling of aryl iodides and disulfides under transition-metal and external photosensitizer free conditions for the synthesis of aryl sulfides at room temperature has been presented, which features mild reaction conditions, broad substrate scope, high efficiency, and good functional group compatibility. The developed methodol. could be readily applied to forge C-S bond in the field of pharmaceutical and material science. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Synthetic Route of C7H9NS).

4-(Methylthio)aniline (cas: 104-96-1) 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.Synthetic Route of C7H9NS

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

Nickel-Catalyzed Reductive Cross-Coupling of (Hetero)Aryl Iodides with Fluorinated Secondary Alkyl Bromides was written by Li, Xuefei;Feng, Zhang;Jiang, Zhong-Xing;Zhang, Xingang. And the article was included in Organic Letters in 2015.HPLC of Formula: 20485-41-0 This article mentions the following:

A mild and efficient nickel-catalyzed reductive cross-coupling between fluorinated secondary alkyl bromides and (hetero)aryl iodides is described. The use of FeBr₂ as an additive successfully overcomes the hydrodebromination and β-fluorine elimination of fluorinated substrates and allows the efficient synthesis of a wide range of trifluoromethyl and difluoroalkyl containing aliphatic compounds with a fluoroalkyl substituted tertiary carbon center. The notable features of this protocol are the synthetic and operational simplicity without preparation of moisture sensitive organometallic reagents and excellent functional group compatibility, even toward active proton containing substrates. In the experiment, the researchers used many compounds, for example, 4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0HPLC of Formula: 20485-41-0).

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) 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.HPLC of Formula: 20485-41-0

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

3,5-bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one was written by Kalogirou, Andreas S.;Koutentis, Panayiotis A.. And the article was included in Molbank in 2019.Application In Synthesis of 2-(Tributylstannyl)thiazole This article mentions the following:

Stille coupling of 3,5-bis(5-bromothien-2-yl)-4H-1,2,6-thiadiazin-4-one (10) with 2-(tri-n-butylstannyl)thiazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110°C, for 2 h, gave 3,5-bis[5-(thiazol-2-yl)thien-2-yl]-4H-1,2,6-thiadiazin-4-one (9) in 81% yield. The latter is evaluated for its electronic properties. In the experiment, the researchers used many compounds, for example, 2-(Tributylstannyl)thiazole (cas: 121359-48-6Application In Synthesis of 2-(Tributylstannyl)thiazole).

2-(Tributylstannyl)thiazole (cas: 121359-48-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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 2-(Tributylstannyl)thiazole

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

KuQuinone as a Highly Stable and Reusable Organic Photocatalyst in Selective Oxidation of Thioethers to Sulfoxides was written by Forchetta, Mattia;Sabuzi, Federica;Stella, Lorenzo;Conte, Valeria;Galloni, Pierluca. And the article was included in Journal of Organic Chemistry in 2022.Synthetic Route of C7H9NS This article mentions the following:

A chemoselective photocatalytic system to perform oxidation of thioethers to sulfoxides RS(O)R¹ [R = nBu, Ph, Bn, etc.; R¹ = Me, Ph, Bn, etc.] was presented. The light-induced oxidation process was here promoted by a metal-free quinoid catalyst, namely 1-hexylKuQuinone (KuQ). Reactions performed in a fluorinated solvent (i.e., HFIP), using O₂ as the oxidant, at room temperature, lead to complete thioanisole conversion to Me Ph sulfoxide in 60 min. Remarkably, the system could be recharged and recycled without a loss of activity and selectivity, reached to turnover numbers (TONs) higher than 4000. Excellent catalytic performances and full selectivity was also been obtained for the photocatalytic oxidation of substituted thioanisole derivatives, aliphatic, cyclic and diaryl thioethers. Likewise, the oxidation of heteroaromatic organosulfur compounds could be accomplished with longer reaction times. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Synthetic Route of C7H9NS).

4-(Methylthio)aniline (cas: 104-96-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The 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.Synthetic Route of C7H9NS

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

Halides Held by Bifurcated Chalcogen-Hydrogen Bonds. Effect of μ_(S,N-H)Cl Contacts on Dimerization of Cl(carbene)Pd^II Species was written by Mikherdov, Alexander S.;Novikov, Alexander S.;Kinzhalov, Mikhail A.;Boyarskiy, Vadim P.;Starova, Galina L.;Ivanov, Alexander Yu.;Kukushkin, Vadim Yu.. And the article was included in Inorganic Chemistry in 2018.Synthetic Route of C9H7ClN2S This article mentions the following:

Addition of 2-thiazolamines with palladium bis-isonitrile complex cis-[PdCl₂(CNCy)₂] (1) produces acyclic diaminocarbene complexes I (R¹ = Ph, 4-MeC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 3,4-F₂C₆H₃; R² = H), dimerized by hydrogen bonds. The reaction of 1 with thiazol-2-amines leads to the C,N-chelated diaminocarbene-like complexes [PdCl{C(N(H)4,5-R₂-thiazol-2-yl)NHCy}(CNCy)] in the case of 4,5-R₂-thiazol-2-amines or gives the diaminocarbene species I for the reaction with 4-aryl-substituted thiazol-2-amines. Inspection of the single-crystal X-ray diffraction data for I suggests that the structures of all these species exhibit previously unrecognized bifurcated chalcogen-hydrogen bonding μ_(S,N-H)Cl and also Pd^II···Pd^II metallophilic interactions. These noncovalent interactions collectively connect two sym. located mols. resulting in their solid-state dimerization. The existence of the μ_(S,N-H)Cl system and its strength (6-9 kcal/mol) were addnl. verified/estimated by a Hirshfeld surface anal. and DFT calculations combined with a topol. anal. of the electron d. distribution within the formalism of Bader’s theory (AIM method) and NBO anal. The observed noncovalent interactions are jointly responsible for the dimerization of I not only in the solid phase but also in CHCl₃ solutions, as predicted theor. by DFT calculations and confirmed exptl. by FTIR, HRESI-MS, ¹H NMR, and diffusion coefficient NMR measurements. Available CCDC data were processed under the new moiety angle, and the observed μ_(S,E-H)Cl systems were classified accordingly to E (E = N, O, C) type atoms. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Synthetic Route of C9H7ClN2S).

4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3) 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. 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.Synthetic Route of C9H7ClN2S

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

Design, synthesis and biological activity of tetrazole-bearing uric acid transporter 1 inhibitors was written by Cai, Wenqing;Liu, Wei;Xie, Yafei;Wu, Jingwei;Liu, Yuqiang;Liu, Changying;Xu, Weiren;Tang, Lida;Wang, Jianwu;Zhao, Guilong. And the article was included in Chemical Research in Chinese Universities in 2017.Category: thiazole This article mentions the following:

Systematic structure-activity relationship(SAR) exploration of a moderately active tetrazole-bearing lesinurad-based hit 1f led to the discovery of a potent uric acid transporter 1(URAT1) inhibitor 1i, which possessed a novel mol. skeleton and was 11-fold more potent than the parent lesinurad against human URAT1 in-vitro (IC₅₀=0.66 μmol/L for 1i vs. 7.18 μmol/L for lesinurad). In the experiment, the researchers used many compounds, for example, 5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (cas: 878671-96-6Category: thiazole).

5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (cas: 878671-96-6) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles was written by Xie, Zengyang;Chen, Ruijiao;Ma, Mingfang;Kong, Lingdong;Liu, Jun;Wang, Cunde. And the article was included in Applied Organometallic Chemistry in 2019.Application of 15864-32-1 This article mentions the following:

An efficient and practical C-N bond formation methodol. for the synthesis of N-(alkyl)benzothiazoles I [R = H, 4-Me, 6-Br, etc.; R¹ = n-Pr, Ph, 4-MeOC₆H₄, etc.] and N-(alkyl)thiazoles II [R² = H, Me; R³ = Ph, 2-MeC₆H₄, 2-naphthyl, etc.; R²R³ = (CH₂)₅; R⁴ = H, 4-Me, 5-Me] was developed via Cu-catalyzed one-pot two-step cross-coupling of 2-aminobenzothiazoles/2-aminothiazoles and aldehydes/ketones with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups. A variety of functionalized benzothiazoles/thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-6-bromobenzothiazole (cas: 15864-32-1Application of 15864-32-1).

2-Amino-6-bromobenzothiazole (cas: 15864-32-1) 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. 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 of 15864-32-1

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

Crystalline vitamin B₁. XIII. Ultraviolet absorption of some derivatives of the basic cleavage product and their synthetic analogs was written by Ruehle, A. E.. And the article was included in Journal of the American Chemical Society in 1935.Recommanded Product: 20485-41-0 This article mentions the following:

The ultraviolet absorption of the basic cleavage product of vitamin B₁ is not only similar to that of the thiazoles but its derivatives exhibit absorption similar to that of corresponding thiazole derivatives Curves are given for the basic product, 4-methyl-, 2,4-dimethyl- and 2-hydroxy-4-methylthiazole HCl salts, 4-methylthiazole-EtI, 4-methylthiazole-5- carboxylic acid and the Cl derivative of the basic product. In the experiment, the researchers used many compounds, for example, 4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0Recommanded Product: 20485-41-0).

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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: 20485-41-0

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