17385-69-2

Basic information

• Product Name: 2-BENZYLAMINO-THIAZOL-4-ONE
• Synonyms: 2-(benzylamino)-1,3-thiazol-4-one
• CAS NO: 17385-69-2
• Molecular Formula: C₁₀H₁₀N₂OS
• Molecular Weight: 0
• Mol File: 17385-69-2.mol

Chemical Properties

• Boiling Point: 352.2°Cat760mmHg
• Flash Point: 166.8°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 3.91E-05mmHg at 25°C
• Refractive Index: 1.661
• CAS DataBase Reference: 2-BENZYLAMINO-THIAZOL-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLAMINO-THIAZOL-4-ONE(17385-69-2)
• EPA Substance Registry System: 2-BENZYLAMINO-THIAZOL-4-ONE(17385-69-2)

Safety Data

• Hazardous Substances Data: 17385-69-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10N2OS/c13-9-7-14-10(12-9)11-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12,13)

Upstream product

• 96-34-4 methyl chloroacetate 
• 621-83-0 N-benzylthiourea 
• 79-11-8 chloroacetic acid 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 100-46-9 benzylamine 
• 622-78-6 Benzyl isothiocyanate 
• 20949-66-0 2-methylsulfanyl-thiazol-4-one 
• 105-39-5 chloroacetic acid ethyl ester 
• 2564-06-9 N-benzyl-2-chloroacetamide 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 107151-64-4 2-benzylamino-5-(2,4-dihydroxy-benzylidene)-thiazol-4-one 
• 332109-24-7 5-(4-hydroxyphenylmethylene)-2-benzylimino-4-oxothiazolidine 
• 76979-43-6 5-(4-Methoxyphenylmethylene)-2-(phenylmethylimino)-4-thiazolidinone 

Relevant articles and documents

SO2F2-Mediated N-Alkylation of Imino-Thiazolidinones

The N-alkylation of ambident and weakly nucleophilic imino-thiazolidinones has been developed via substitution with alkyl fluorosulfonates. These reactive electrophiles are obtained through the transformation of nontoxic, economic, and commercially availa

Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies

Here-in, we present molecular design, chemical synthesis and evaluation of novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors. The newly synthesized compounds were evaluated for their in vitro cytotoxicities against A549 (lung cancer), MDA-MB-231 and BT-471 (breast cancer), HepG2 (liver cancer) and HCT-116 (colon cancer) cell lines by MTT assay. Among the synthesized compounds, compound 12b showed excellent anticancer activity on MDA-MB-231 cell line with IC50 value of 0.95 ± 1.88 μM and was verified to be safe in normal human bronchial epithelial cells (Beas-2B). Apoptosis induced by the lead 12b was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 12b induced early apoptosis. Additionally, cell cycle analysis indicated that the MDA-MB-231 cells were arrested at sub-G2/M phase and also inhibited tubulin polymerization with IC50 value of 3.54 ± 0.2 μM. Molecular docking simulations were employed to identify the important binding modes responsible for the tubulin inhibitory activity, thus supporting their effective anticancer potential.

Discovery of certain benzyl/phenethyl thiazolidinone-indole hybrids as potential anti-proliferative agents: Synthesis, molecular modeling and tubulin polymerization inhibition study

A series of certain benzyl/phenethyl thiazolidinone-indole hybrids were synthesized for the study of anti-proliferative activity against A549, NCI-H460 (lung cancer), MDA-MB-231 (breast cancer), HCT-29 and HCT-15 (colon cancer) cell lines by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). We found that compound G37 displayed highest cytotoxicity with IC50 value of 0.92 ± 0.12 μM towards HCT-15 cancer cell line among all the synthesized compounds. Moreover, compound G37 was also tested on normal human lung epithelial cells (L132) and was found to be safe in contrast to HCT-15 cells. The lead compound G37 showed significant G2/M phase arrest in HCT-15 cells. Additionally, compound G37 significantly inhibited tubulin polymerization with IC50 value of 2.92 ± 0.23 μM. Mechanistic studies such as acridine orange/ethidium bromide (AO/EB) dual staining, DAPI nuclear staining, annexinV/propidium iodide dual staining, clonogenic growth inhibition assays inferred that compound G37 induced apoptotic cell death in HCT-15 cells. Moreover, loss of mitochondrial membrane potential with elevated intracellular ROS levels was observed by compound G37. These compounds bind at the active pocket of the α/β-tubulin with higher number of stable hydrogen bonds, hydrophobic and arene-cation interactions confirmed by molecular modeling studies.

Design, synthesis and biological evaluation of 5-benzylidene-2-iminothiazolidin-4-ones as selective GSK-3β inhibitors

In this work, iminothiazolidin-4-one derivatives were explored as selective GSK-3β inhibitors. Molecular docking analysis was carried to design a series of compounds, which were synthesized using substituted thiourea, 2-bromoacetophenones and benzaldehydes. Out of the twenty five compounds synthesized during this work, the in?vitro evaluation against GSK-3 led to the identification of nine compounds with activity in lower nano-molar range (2–85?nM). Further, in?vitro evaluation against CDK-2 showed five compounds to be selective towards GSK-3.

Synthesis and activity of quinolinyl-methylene-thiazolinones as potent and selective cyclin-dependent kinase 1 inhibitors

A novel series of quinolinyl-methylene-thiazolinones has been identified as potent and selective cyclin-dependent kinase 1 (CDK1) inhibitors. Their synthesis and structure activity relationships (SAR) are described. Representative compounds from this class reversibly inhibit CDK1 activity in vitro, and block cell cycle progression in human tumor cell lines, suggesting a potential use as antitumor agents.