Heterocyclic Building Blocks-Thiazole

Design and Synthesis of a New Series of 4-Heteroarylamino-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octanes as α7 Nicotinic Receptor Agonists. 1. Development of Pharmacophore and Early Structure-Activity Relationship was written by Cook, James;Zusi, F. Christopher;McDonald, Ivar M.;King, Dalton;Hill, Matthew D.;Iwuagwu, Christiana;Mate, Robert A.;Fang, Haiquan;Zhao, Rulin;Wang, Bei;Cutrone, Jingfang;Ma, Baoqing;Gao, Qi;Knox, Ronald J.;Matchett, Michele;Gallagher, Lizbeth;Ferrante, Meredith;Post-Munson, Debra;Molski, Thaddeus;Easton, Amy;Miller, Regina;Jones, Kelli;Digavalli, Siva;Healy, Francine;Lentz, Kimberley;Benitex, Yulia;Clarke, Wendy;Natale, Joanne;Siuciak, Judith A.;Lodge, Nicholas;Zaczek, Robert;Denton, Rex;Morgan, Daniel;Bristow, Linda J.;Macor, John E.;Olson, Richard E.. And the article was included in Journal of Medicinal Chemistry in 2016.Safety of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

The design and synthesis of quinuclidine-containing spirooxazolidines (spiroimidates) and their utility as α7 nicotinic acetylcholine receptor partial agonists are described. Selected members of the series demonstrated excellent selectivity for α7 over the highly homologous 5-HT_3A receptor. Modification of the N-spiroimidate heterocycle substituent led to ((1S,2R,4S)-N-isoquinolin-3-yl)-4’H-4-azaspiro[bicyclo[2.2.2]octane-2,5’oxazol]-2′-amine (BMS-902483), a potent α7 partial agonist, which improved cognition in preclin. rodent model. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Safety of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

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

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

Halogenated 2′-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions was written by Stanetty, Peter;Schnuerch, Michael;Mihovilovic, Marko D.. And the article was included in Journal of Organic Chemistry in 2006.COA of Formula: C9H6ClNS This article mentions the following:

Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biol. activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3COA of Formula: C9H6ClNS).

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). 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: C9H6ClNS

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

Novel 12N-substituted matrinanes as potential anti-coxsackievirus agents was written by Li, Ying-Hong;Tang, Sheng;Li, Yu-Huan;Cheng, Xin-Yue;Zhang, Xin;Wang, Yan-Xiang;Su, Feng;Song, Dan-Qing. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

A series of novel 12N-substituted matrinane derivatives were synthesized and evaluated for their activities against coxsackievirus type B3 (CVB3) taking compound I as the lead. SAR anal. indicated that the introduction of a suitable heteroaromatic ring on the 12N-atom might be beneficial for the activity. Among them, compound II exhibited the highest potency against all CVB serotypes as well as CVA16 with IC₅₀ values ranging from 2.02 μM to 7.41 μM, indicating a broad-spectrum anti-coxsackieviruse effect. Furthermore, compound II demonstrated a good safety profile in vivo. Thus, we consider 12N-substituted matrinanes to be a promising family of anti-coxsackievirus agents, and compound II to be a promising drug candidate in the treatment of various diseases related to coxsackievirus infection. 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. 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Electric Literature of C6H7ClN2O3S2

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

A convenient synthesis of 2-mercapto- and 2-chlorobenzothiazoles was written by Zhu, Lei;Zhang, Mingbao;Dai, Miao. And the article was included in Journal of Heterocyclic Chemistry in 2005.Application of 80945-86-4 This article mentions the following:

A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-Et dithiocarbonate under mild conditions. Subsequent intra-mol. cyclization affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily converted to corresponding 2-chlorobenzothiazoles upon treatment with sulfuryl chloride. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Application of 80945-86-4).

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

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

The scope and limitations of deuteration mediated by Crabtree’s catalyst was written by Ellames, George J.;Gibson, Jennifer S.;Herbert, John M.;McNeill, Alan H.. And the article was included in Tetrahedron in 2001.Recommanded Product: 5-Phenylthiazole This article mentions the following:

Exchange of protons for deuterons mediated by Crabtree’s catalyst is directed efficiently by a functional group containing an sp²-hybridized nitrogen or oxygen atom; more electron-rich substrates are, in general, deuterated more efficiently. The electronic effects of substituents in the arene ring are critical only where the directing group is poor, in which case exchange is generally promoted by electron donating substituents, but the exchange is impeded by bulky meta-substituents. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 5-Phenylthiazole

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

High-Yield Synthesis of Pyridyl Conjugated Microporous Polymer Networks with Large Surface Areas: From Molecular Iodine Capture to Metal-Free Heterogeneous Catalysis was written by Zuo, Hongyu;Wei, Lyu;Zhang, Weiyi;Li, Ying;Liao, Yaozu. And the article was included in Macromolecular Rapid Communications in 2020.Formula: C13H10N2S This article mentions the following:

Capturing volatile radioactive nuclides including iodine (I129 or I131) is one of the major problems to be solved for environmental sustainability. Multiple types of functional microporous materials such as metal organic frameworks and covalent organic frameworks have been constructed for iodine emission control. However, most of the microporous materials are limited by their weak binding force with iodine and low stability, leading to low capture efficiencies. Herein, the synthesis of pyridyl conjugated microporous polymer networks with large surface areas (PCMP-Y) up to 1304 m2 g-1 and high yields up to 95% via a simple Yamamoto cross-coupling reaction, is reported. The PCMP-Y carries amine and pyridine N groups which have stronger interactions with iodine mols. The high sp. surface areas and porosities of PCMP-Y facilitate iodine capture, delivering a maximum adsorption capacity of 4.75 g g-1 in a short time (3 h), which is superior to a majority of porous materials reported. Moreover, the reversible desorption nature of PCMP-Y capturing iodine imparts a platform for metal-free heterogeneous catalyst, which can be applied to synthesize aminobenzothiazole medicines via O2-promoted cascade reactions. 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. 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.Formula: C13H10N2S

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

Thiazole derivatives as vulcanization accelerators. II-IV was written by Kimijima, Takuzo;Miyama, Shunichi. And the article was included in Kogyo Kagaku Zasshi in 1943.Product Details of 1843-21-6 This article mentions the following:

Equivalent amounts of PhNH₂, CS₂, and S were made to react in an autoclave under pressure at 180-260° for 6 hrs. to obtain mercaptobenzothiazole, with the pressure varying from 20 to 50 atm. according to the temperature used. Analysis showed that at 180° the reaction was incomplete, the product being mostly anilinobenzothiazole with a large amount of aniline left unreacted. Yields of mercaptobenzothiazole at 200, 220, 240, and 260° of 13.3, 86.5, 76.4, and 67.6%, resp., were obtained. From the reaction products at various temperatures, it was deduced that mercaptobenzothiazole is formed through anilinobenzothiazole and that the reaction is endothermic. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Product Details of 1843-21-6).

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. 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.Product Details of 1843-21-6

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

Design, synthesis, and structure-activity relationships of unsubstituted piperazinone-based transition state factor Xa inhibitors was written by Huang, Wenrong;Naughton, Mary Ann;Yang, Hua;Su, Ting;Dam, Suiko;Wong, Paul W.;Arfsten, Ann;Edwards, Susan;Sinha, Uma;Hollenbach, Stanley;Scarborough, Robert M.;Zhu, Bing-Yan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2003.Formula: C6H7ClN2O3S2 This article mentions the following:

A series of novel transition state factor Xa inhibitors containing a variety of lactam ring systems as central templates was synthesized in an expedient manner and allowed for a great deal of structural variability. Among them, the piperazinone-based inhibitors were found to be not only active against factor Xa but also selective over thrombin. Optimization of the P4 moiety yielded several potent compounds with IC₅₀ below 1 nM against factor Xa. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Formula: C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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 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.Formula: C6H7ClN2O3S2

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

Solid-phase synthesis and modification of thiazole orange and its derivatives and their spectral properties was written by Fei, Xuening;Yang, Shaobin;Zhang, Baolian;Liu, Zhijun;Gu, Yingchun. And the article was included in Journal of Combinatorial Chemistry in 2007.Reference of 58759-63-0 This article mentions the following:

A new solid-phase synthesis is shown to be effective in the preparation of the cyanine dye thiazole orange (TO) and its derivatives, which can be obtained as a traceless cleavage of the Merrifield resin method. The influence of different solvents and substituent groups on benzothiazole (such as Cl, Me, and NO₂) was extensively studied. The changes of the spectral characteristics and fluorescence intensity of the TO derivatives were described. The phenomenon of the synergetic effect was also depicted after modifying the TO mol. with chitosan oligosaccharide at the end of the alkyl, which can effectively improve the sensitivity of the fluorescent probe. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Reference of 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Reference of 58759-63-0

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

Synthesis and antimicrobial screening of substituted 2-mercaptobenzothiazoles was written by Murti, Y.;Pathak, D.. And the article was included in Journal of Pharmaceutical Research in 2008.Application In Synthesis of 5-Nitrobenzothiazole-2-thiol This article mentions the following:

The study explores the antimicrobial activity of some 2-mercaptobenzothiazoles and correlates the effect on the antimicrobial potency by varying the substituents in the benzene part of the benzothiazole ring system. Substituted 2-mercaptobenzothiazoles, e.g., I, were prepared by heterocyclization of anilines with carbon disulfide. The synthetic methods used are simple, rapid, and economical and found to be accurate and reproducible. The results of antibacterial and antifungal studies have been found to be satisfactory. Antibacterial activity of the compounds was tested using Escherichia coli, Staphylococcus aureus and Bacillus subtilis and antifungal activity of the compounds was tested using Aspergillus niger and Candida albicans. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Application In Synthesis of 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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 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.Application In Synthesis of 5-Nitrobenzothiazole-2-thiol

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