6244-77-5

Basic information

• Product Name: Benzenecarbothioamide, 4-nitro-N-phenyl-
• CAS NO: 6244-77-5
• Molecular Formula: C13H10N2O2S
• Molecular Weight: 258.301
• Mol File: 6244-77-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzenecarbothioamide, 4-nitro-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarbothioamide, 4-nitro-N-phenyl-(6244-77-5)
• EPA Substance Registry System: Benzenecarbothioamide, 4-nitro-N-phenyl-(6244-77-5)

Safety Data

• Hazardous Substances Data: 6244-77-5(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 122-04-3 4-nitro-benzoyl chloride 
• 317818-11-4 4-nitrobenzoyl (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphinan-2-yl) sulfide 
• 165543-76-0 4-Nitro-dithiobenzoic acid 4-bromo-phenyl ester 
• 165543-82-8 4-Nitro-dithiobenzoic acid 4-chloro-phenyl ester 
• 165543-80-6 4-Nitro-dithiobenzoic acid p-tolyl ester 
• 112303-01-2 4-Nitrodithiobenzoesaeurephenylester 
• 3460-11-5 4-nitrobenzanilide 

Downstream Products

• 25309-95-9 Benzyl-<4-nitro-α-phenylimino-benzyl>-disulfid 
• 3460-11-5 4-nitrobenzanilide 
• 6278-73-5 2-(4-aminophenyl)benzothiazole 
• 52214-61-6 2-(4-Azidophenyl)benzothiazole 
• 1458715-44-0 2-(4-(2-methyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-43-9 2-(4-(2-methyl-5-(4-nitrophenyl)-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-42-8 2-(4-(2-(4-methoxyphenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-41-7 2-(4-(2-(4-fluorophenyl)-5-methyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-40-6 2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 136169-28-3 C₁₄H₁₃N₅O₂S 
• 22868-34-4 2-(4-nitrophenyl)benzothiazole 
• 3333-52-6 2,2,3,3-tetramethylsuccinonitrile 
• 25325-80-8 <4-Nitro-α-phenylimino-benzyl>-phenyl-disulfid 
• 25309-96-0 tert-Butyl-<4-nitro-α-phenylimino-benzyl>-disulfid 

Relevant articles and documents

Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights

A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4?hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures of the synthesized compounds were characterized based on their spectral (IR, 1H NMR, 13C NMR and MS) and elemental analysis. The cytotoxicity screening studies revealed that MCF-7 and WRL68 cancer cells were sensitive to all the tested compounds. Out of twelve novel hybrids, compound 8f displayed the most significant anticancer activity. Docking studies were performed in order to understand the binding mode of the title compounds at the active site of the target enzyme (EGFR tyrosine kinase, 1M17). Compounds 8f and 7f displayed prominent and conserved binding interactions against 1M17. In addition, compounds 7e, 7f, 8e, and 8f exhibited interesting in vitro antibacterial activity, especially against Gram-negative bacteria E. coli. In summary, the novel benzo[d]thiazolyl substituted-2-quinolone hybrid (8f) could be considered as promising hit and could be further exploited for developing potential anticancer/antimicrobial agents.

Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.

SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF

The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R1 of formulae 1-6 is H, C1-10 alkyl, C1-10 alkoxy or C1-10 haloalkyl, and R2 of formulae 1-6 is H or C1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R1 and R2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.