57493-24-0

Basic information

• Product Name: 4-(3-NITRO-PHENYL)-THIAZOL-2-YLAMINE
• Synonyms: AKOS BC-0568;AKOS BBS-00004741;OTAVA-BB BB0108540042;TOSLAB 566071;4-(3-nitrophenyl)-1,3-thiazol-2-ylamine;4-(3-nitrophenyl)thiazol-2-amine;2-Amino-4-(3-nitrophenyl)-1,3-thiazole;2-AMino-4-(3-nitrophenyl)thiazole
• CAS NO: 57493-24-0
• Molecular Formula: C₉H₇N₃O₂S
• Molecular Weight: 221.24
• Product Categories: Amines;Thiazoles, Isothiazoles & Benzothiazoles
• Mol File: 57493-24-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 189-191 °C
• Boiling Point: 447.2 °C at 760 mmHg
• Flash Point: 224.2 °C
• Appearance: /
• Density: 1.459 g/cm³
• Vapor Pressure: 3.44E-08mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.54±0.10(Predicted)
• CAS DataBase Reference: 4-(3-NITRO-PHENYL)-THIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-NITRO-PHENYL)-THIAZOL-2-YLAMINE(57493-24-0)
• EPA Substance Registry System: 4-(3-NITRO-PHENYL)-THIAZOL-2-YLAMINE(57493-24-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 57493-24-0(Hazardous Substances Data)

Usage

General Description

4-(3-Nitro-phenyl)-thiazol-2-ylamine is a chemical compound with the molecular formula C9H7N3O2S. It is commonly used in the pharmaceutical industry as a building block for the synthesis of various biologically active compounds. This chemical has a thiazole ring and a nitrophenyl group, which can impart unique properties to the molecules it is incorporated into. Thiazole derivatives have been studied for their potential as antimicrobial, antiviral, and anticancer agents, and 4-(3-nitro-phenyl)-thiazol-2-ylamine may serve as a valuable intermediate in the development of new drugs with these activities. Additionally, this compound may also find applications in agrochemicals and material science due to its structural features. Overall, the synthesis and characterization of 4-(3-nitro-phenyl)-thiazol-2-ylamine are important in the field of organic chemistry and pharmaceutical research.

InChI:InChI=1/C9H7N3O2S/c10-9-11-8(5-15-9)6-2-1-3-7(4-6)12(13)14/h1-5H,(H2,10,11)

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Downstream Products

• 79652-50-9 7-{[4-(3-Nitro-phenyl)-thiazol-2-ylamino]-phenyl-methyl}-quinolin-8-ol 
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Relevant articles and documents

Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds 7c, 7d and 7e exhibited significant antiproliferative activities at 10?5 M dose. Compound 7c exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, compound 7d showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. Compound 7c inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival. The flow cytometric analysis showed that 7c displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. Compound 7c clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-positive and Gram-negative as well as Candida albicans. Only compound 7d exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound.

Synthesis and Molecular Docking Studies of Some 1,2-Dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydroquinazolin-4(1H)-ones as Anticancer Agents

Synthesis of 1, 2-dimethyl-3(4-substituted phenyl-1,3-thiazol-2-yl)2,3-dihydro quinazolin-4(1H)-ones (5Aa1-5Ak11) derivatives was effected by refluxing 1,2-dimethylbenzoxazine-4-one with different 4-substituted phenyl-1,3-thiazol-2-amines. Synthesized compounds were characterized through elemental analysis, infrared, proton nuclear magnetic resonance, and Carbon-13 nuclear magnetic resonance. Molecular docking studies were carried out using Schr?dinger Glide (version 2020_1) which was docked into selective P38alpha and Activin A Receptor Type 1 (ACVR1) Activin receptor-like kinase-2 (ALK2) kinase with Protein Data Bank (PDB) code 3GC7, 6GI6. Based on the docking score of synthesized quinazolin-4-one derivatives, co-crystallized ligands interaction was evaluated with 5-fluorouracil (5-FU) as a reference drug. Compounds 5Ae5, 5Aa1, 5Ai9, and 5Ab2 with P38alpha, 5Af6, 5Ae5, 5Ad4, and 5Ab2 with ACVR1 (ALK2) kinase score were -7.265, -7.078, -7.058, and -6.836; -8.929, -8.749, -8.735, and -8.464 Kcal/mol against enzymes responsible for cancer treatment. The results indicated that quinazolin-4-one derivatives had scored better than ligand and 5-FU.

Design, synthesis and molecular modelling studies of 1-methyl-3-(4-substituted phenyl-1,3thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1h)-ones as potent anticancer agents

The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4-substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcinoma based on molecular docking studies on 3GC7-the structure of p38alpha in complex with dihydroquinazolinone. Finally, compounds 5Dh8, 5DF6, 5Db2 and 5Di9 exhibited better activity at a concentration 10 μg/mL when compared to 5-fluorouracil. The ADME properties revealed that all the compounds were within the range and docking studies showed the highest binding with glide score -7.19 and -7.027 Kcal/mol compared to the target protein -10.67 Kcal/mol.