43087-91-8

Usage

Safety Profile

Moderately toxic by ingestion.Severe eye irritant. When heated to decomposition it emitsvery toxic fumes of NOx and SOx.

InChI:InChI=1/C13H10N2S/c14-10-6-7-12-11(8-10)15-13(16-12)9-4-2-1-3-5-9/h1-8H,14H2

Upstream product

• 35539-24-3 S-2,4-dinitrophenyl thiobenzoate 
• 64448-50-6 5-nitro-2-phenyl-benzothiazole 
• 4826-10-2 6-nitro-3-phenyl-2H-benzo[e][1,2,4]thiadiazine 1-oxide 
• 21715-13-9 2,4-diaminobenzenethiol 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 205827-96-9 N-(2-chloro-5-nitro-phenyl)-benzamide 
• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 16239-26-2 N-3-nitrophenylbenzamidine 
• 4826-02-2 6-nitro-3-phenyl-1-(toluene-4-sulfonylamino)-1λ⁴-benzo[1,2,4]thiadiazine 
• 857950-75-5 bis-(4-acetylamino-2-amino-phenyl)-disulfide 
• 74804-14-1 bis(4-acetylamino-2-nitrophenyl) disulphide 
• 5540-60-3 N-(4-chloro-3-nitrophenyl)acetamide 
• 860521-46-6 thiobenzoic acid-(3-nitro-anilide) 

Downstream Products

• 1346678-91-8 2-{(E)-[(2-phenyl-1,3-benzothiazol-5-yl)imino]methyl}benzene-1,4-diol 
• 13399-20-7 2,7-diphenyl-benzo[1,2-d;3,4-d']bisthiazole 

Relevant academic research and scientific papers

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.

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.

TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY

There are disclosed compound of Formula (1): A1, A2, A3 and A4 which may be the same or different, represent N or CR1, X is a divalent group selected from O, S(O)n, C=W, NR4, NC(=O)R5 and CR6R7, W is O, S, NR20, Y is N or CR8, one of R4, R5, R6, R8, R9 and NR20 represents - L -R3, in which L is a single bond or a linker group, additionally, R1, R3 - R9, which may be the same or different, independently represent hydrogen or a substituent and R20 represents hydrogen, hydroxyl, alkyl optionally substituted by aryl, alkoxy optionally substituted by aryl, aryl, CN, optionally substituted alkoxy, optionally substituted aryloxy, optionally substitute alkanoyl, optionally substituted aroyl, NO2, NR30R31, in which R30 and R31, which may be the same or different, represent hydrogen, optionally substituted alkyl or optionally substituted aryl; additionally, one of R30 and R31 may represent optionally substituted alkanoyl or optionally substituted aroyl, n represents an integer from 0 to 2, in addition, when an adjacent pair of A1 - A4 each represent CR1, then the adjacent carbon atoms, together with their substituents may form a ring B, when X is CR6R7, R6 and R7, together with the carbon atom to which they are attached may form a ring C, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the therapeutic and/or prophylactic treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia.

Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which:G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; andZ is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.

Novel anti-inflammatory and analgesic heterocyclic amidines that inhibit nitrogen oxide (NO) production

Heterocyclic amidines with anti-inflammatory and analgesic activity that inhibit nitrogen oxide production, of formula (I): in which: G1 and G2 are hydrogen, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, and an amidino substituent of formula Q, provided that, for each compound of formula (I), only one of the two substituents G1 or G2 is an amidino substituent of formula Q: and in which the substituents W, Y and X are combined to form 9- or 10-membered bicyclic heteroaromatic derivatives containing up to 2 hetero atoms in the same ring; and Z is an aryl or heteroaryl group, a linear or branched C1-C6 alkyl or alkenyl chain, a C1-C4 alkyl-aryl group or a C1-C4 alkyl-heteroaryl group.