1123-93-9

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Benzothiazol-5-amine is used as a pharmaceutical intermediate for the synthesis of various drugs and drug candidates. Its unique structure and reactivity make it a valuable building block in the development of new therapeutic agents.
Used in Allosteric Enhancer Development:
1,3-Benzothiazol-5-amine is used as an allosteric enhancer (AE) of agonist activity at the A1 adenosine receptor. This application is particularly relevant in the development of drugs targeting the central nervous system, as modulation of the A1 adenosine receptor can have therapeutic effects in conditions such as epilepsy, neurodegenerative diseases, and cognitive disorders. By enhancing the activity of agonists at this receptor, 1,3-benzothiazol-5-amine can potentially improve the efficacy and selectivity of these drugs.

InChI:InChI=1/C7H6N2S/c8-5-1-2-7-6(3-5)9-4-10-7/h1-4H,8H2

Upstream product

• 58759-63-0 5-nitrobenzo[d]thiazole-2(3H)-thione 
• 2942-07-6 5-nitrobenzothiazole 
• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 53666-48-1 N-(2-chloro-5-nitrophenyl)formamide 
• 21715-13-9 2,4-diaminobenzenethiol 
• 122-51-0 orthoformic acid triethyl ester 
• 10403-47-1 2-bromo 5-nitroaniline 
• 98556-09-3 N-(2-bromo-5-nitrophenyl)formamide 
• 97-00-7 1-chloro-2,4-dinitro-benzene 

Downstream Products

• 769-19-7 4-bromobenzo[d]thiazol-5-amine 
• 744261-37-8 N-benzothiazol-5-yl-6-(4-fluorophenyl)-2-methylnicotinamide 
• 256415-35-7 C₁₄H₁₁N₃S₂ 
• 1360449-09-7 1,3-di(benzo[d]thiazol-5-yl)thiourea 
• 36894-62-9 N-phenylbenzo[d]thiazol-5-amine 
• 1037758-58-9 C₂₄H₂₀N₄O₄S₂ 
• 1037763-45-3 C₂₅H₂₂N₄O₄S₂ 
• 1037763-41-9 C₂₆H₂₃N₃O₃S 
• 1037763-43-1 C₂₄H₁₉N₃O₃S 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities

A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.

ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I" PATHWAY AND METHODS OF USE THEREOF

The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.

ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I' PATHWAY AND METHODS OF USE THEREOF

The present invention is directed to compounds of Formula (I), which are activators of the RIG-I pathway.

Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.

COMPOUNDS FOR TREATMENT OF TRYPANOSOMES AND NEUROLOGICAL PATHOGENS AND USES THEREOF

The present invention relates to novel compounds that cross the blood-brain barrier and are effective inhibitors of neurological pathogens such as trypanosomes. The invention further relates to the use of these compounds for treating disorders related to trypanosomes and neurological pathogens.

Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis

A previous publication from this lab (Patrick, et al. Bioorg. Med. Chem. 2016, 24, 2451-2465) explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole (1), which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogues, were quite potent, these molecules as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogues arising from medicinal chemistry optimization at different sites on the molecule. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analogue, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (57) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.

Iron and palladium(II) phthalocyanines as recyclable catalysts for reduction of nitroarenes

Iron(II) and palladium(II) phthalocyanines have been established as recyclable heterogeneous catalysts for the reduction of aromatic nitro compounds to corresponding amines using diphenylsilane/sodium borohydride as hydrogen sources in ethanol. Various reducible functional groups, such as acetyl, ester, cyano, amide, sulphonamide and carboxylic acid etc. were well tolerated, and the methods were applicable up to gram scale. Mechanistic studies showed that reduction of nitro group proceed through direct (nitroso) pathway and possibly iron or palladium phthalocyanines activates nitro group for reduction. FePc and PdPc also catalyzed the generation of hydrogen from the combination of diphenylsilane/sodium borohydride and ethanol.

ESTROGEN RECEPTOR MODULATORS AND USES THEREOF

Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

Structure-activity relationships of N-phenyl-N′-benzothiazol-6-ylurea synthetic derivatives: Cytokinin-like activity and adventitious rooting enhancement

Some years ago we demonstrated the cytokinin-like activity of the synthetic N-phenyl-N′-benzothiazol-6-ylurea (PBU) and a relevant adventitious rooting adjuvant activity of symmetric urea derivatives devoid of any cytokinin- or auxin-like activity per se. Here we report the synthesis and the biological activity evaluation of nine symmetric or asymmetric ureas/thioureas, structurally related to PBU. None of them show cytokinin-like activity, while we demonstrate for the first time that PBU interacts with Arabidopsis cytokinin receptor CRE1/AHK4 in a heterologous bioassay system. Among the PBU derivatives, all the symmetric ureas/thioureas show an adventitious rooting adjuvant activity in various bioassays, confirming that this activity is strictly dependent on their chemical structure.

USE OF TRIFLUOROMETHYL SUBSTITUTED BENZAMIDES IN THE TREATMENT OF NEUROLOGICAL DISORDERS

The invention relates to methods of using the compounds of the invention, including trifluoromethyl substituted benzamide compounds and salts thereof, as well as pharmaceutical compositions comprising the same, in the treatment of Eph receptor-related (e.g., neurological) injuries and disorders. The invention also relates to modulating the activity of an Eph receptor in a cell, stimulating neural regeneration, and reversing neuronal degeneration, by administering a compound of the invention to a cell or subject in an effective amount.