Xu, Hui et al. published their research in ACS Catalysis in 2021 | CAS: 68867-17-4

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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.Name: Benzothiazole-5-carboxylic acid

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products was written by Xu, Hui;Ma, Biao;Fu, Zunyun;Li, Han-Yuan;Wang, Xing;Wang, Zhen-Yu;Li, Ling-Jun;Cheng, Tai-Jin;Zheng, Mingyue;Dai, Hui-Xiong. And the article was included in ACS Catalysis in 2021.Name: Benzothiazole-5-carboxylic acid This article mentions the following:

A palladium-catalyzed ligand-promoted alkynation of unstrained aryl ketones RC(O)R1 (R = naphthalen-2-yl, 1-benzothiophen-5-yl, 4-(2H-1,2,3-triazol-2-yl)benzen-1-yl, etc.; R1 = Me, n-Pr, Ph, etc.) have been reported. The protocol allows the alkynation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope for the synthesis of aryl-/terminal alkynes RCCR2 (R2 = 2-fluorophenyl, naphthalen-2-yl, thiophen-2-yl, etc.) and RCCH. The potential applications of this protocol in drug discovery and chem. biol. are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products e.g., I. More importantly, two different biol. important fragments R3CCR4 (R = 3-methoxy-4-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy)benzen-1-yl, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalen-2-yl; R4 = 4-(dipropylsulfamoyl)phenyl) derived from a pharmaceutical and natural product could be connected by the consecutive alkynation of ketones CH3(CH2)2C(O)R4. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone (1-[(17β)-17-(acetyloxy)estra-1,3,5(10)-trien-2-yl]ethanone) by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Name: Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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.Name: Benzothiazole-5-carboxylic acid

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

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Described herein are compounds that activate pyruvate kinase R, pharmaceutical compositions and methods of use thereof. These compounds are represented by Formula (I): Formula (I) wherein R’, R2, L’, and L2 are as defined herein.

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Thiazole | C3H7648NS – PubChem,
Thiazole | chemical compound | Britannica

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The present invention relates generally to the field of ligands for nicotinic acetylcholine receptors (nACh receptors), activation of nACh receptors, and the treatment of disease conditions associated with defective or malfunctioning nicotinic acetylcholine receptors, especially of the brain. Further, this invention relates to novel compounds (e.g., indazoles and benzothiazoles), which act as ligands for the alpha7 nACh receptor subtype, methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

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Reference:
Thiazole | C3H7636NS – PubChem,
Thiazole | chemical compound | Britannica

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Aminopiperidine derivatives of formula (I) and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly in man. 1

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Thiazole | C3H7652NS – PubChem,
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The present disclosure provides, in part, cyclic sulfamide compounds, and pharmaceutical compositions thereof, useful as modulators of Hepatitis B (HBV) core protein, and methods of treating Hepatitis B (HBV) infection.

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Discovery of Pyrazolocarboxamides as Potent and Selective Receptor Interacting Protein 2 (RIP2) Kinase Inhibitors

Herein we report the discovery of pyrazolocarboxamides as novel, potent, and kinase selective inhibitors of receptor interacting protein 2 kinase (RIP2). Fragment based screening and design principles led to the identification of the inhibitor series, and X-ray crystallography was used to inform key structural changes. Through key substitutions about the N1 and C5 N positions on the pyrazole ring significant kinase selectivity and potency were achieved. Bridged bicyclic pyrazolocarboxamide 11 represents a selective and potent inhibitor of RIP2 and will allow for a more detailed investigation of RIP2 inhibition as a therapeutic target for autoinflammatory disorders.

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The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D3 Receptor (D3R) Selective Agonists

Because of the large degree of homology among dopamine D2-like receptors, discovering ligands capable of discriminating between the D2, D3, and D4 receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chemical modification of the D3 preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D3R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D3R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D3R binding selectivities than the reference compounds. Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation.

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Thiazole | C3H7651NS – PubChem,
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The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D3 Receptor (D3R) Selective Agonists

Because of the large degree of homology among dopamine D2-like receptors, discovering ligands capable of discriminating between the D2, D3, and D4 receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chemical modification of the D3 preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D3R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D3R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D3R binding selectivities than the reference compounds. Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation.

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Reference:
Thiazole | C3H7651NS – PubChem,
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The present invention provides compounds of formula I which bind to the ubiquitously expressed E3 ligase protein cereblon (CRBN) and alter the substrate specificity of the CRBN E3 ubiquitin ligase complex, resulting in breakdown of intrinsic downstream proteins. Present compounds are thus useful for the treatment of various cancers.

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Thiazole | C3H7638NS – PubChem,
Thiazole | chemical compound | Britannica

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A series of 180 vinblastine 20? amides were prepared in three steps from commercially available starting materials, systematically exploring a typically inaccessible site in the molecule enlisting a powerful functionalization strategy. Clear structure-activity relationships and a structural model were developed in the studies which provided many such 20? amides that exhibit substantial and some even remarkable enhancements in potency, many that exhibit further improvements in activity against a Pgp overexpressing resistant cancer cell line, and an important subset of the vinblastine analogues that display little or no differential in activity against a matched pair of vinblastine sensitive and resistant (Pgp overexpressing) cell lines. The improvements in potency directly correlated with target tubulin binding affinity, and the reduction in differential functional activity against the sensitive and Pgp overexpressing resistant cell lines was found to correlate directly with an impact on Pgp-derived efflux.

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Thiazole | C3H7653NS – PubChem,
Thiazole | chemical compound | Britannica