289686-98-2

Basic information

• Product Name: tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-(4-phenylpiperazin-1-ylmethyl)-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate
• Synonyms: tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-(4-phenylpiperazin-1-ylmethyl)-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate
• CAS NO: 289686-98-2
• Molecular Weight: 612.171
• Mol File: 289686-98-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-(4-phenylpiperazin-1-ylmethyl)-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-(4-phenylpiperazin-1-ylmethyl)-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate(289686-98-2)
• EPA Substance Registry System: tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-(4-phenylpiperazin-1-ylmethyl)-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate(289686-98-2)

Safety Data

• Hazardous Substances Data: 289686-98-2(Hazardous Substances Data)

Upstream product

• 289686-87-9 tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-88-0 tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-85-7 2-acetoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 289686-84-6 2-acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one 
• 458533-73-8 2-methoxyacetamido-4-chloro-5-methyl N-methylbenzamide 
• 458533-71-6 methyl 2-methoxyacetamido-4-chloro-5-methylbenzoate 
• 289686-83-5 7-chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one 
• 458533-75-0 2-methoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 458533-77-2 2-hydroxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 458533-67-0 7-chloro-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 458533-69-2 methyl 2-amino-4-chloro-5-methylbenzoate 
• 289686-80-2 2-cyano-5-chloro-4-methylaniline 
• 95-74-9 3-chloro-p-toluidine 
• 155184-81-9 2-amino-5-methyl-4-chlorobenzoic acid 

Relevant articles and documents

The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent

4-[N-[7-Bromo-2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl] -N-(prop-2-ynyl)amino]-N-(3-pyridylmethyl)benzamide (CB30865) is a quinazolin-4-one antitumor agent whose high growthinhibitory activity (W1L2 IC50 = 2.8 ± 0.50 nM) is believed to have a folate-independent locus of action. In addition, CB30865 represents a class of compounds with unique biochemical characteristics such as a delayed, non-phase specific, cell-cycle arrest. The low aqueous solubility of CB30865 prompted a search for more water-soluble analogues for in vivo evaluation of this class of compounds. It was thought that aqueous solubility could be increased by the introduction of amino functionalities at the 2-position of the quinazolin-4-one ring. A variety of compounds (5a-j, 31a-c, 32, and 33) were synthesized in a linear fashion starting from 3-chloro-4-methylaniline. Most of these compounds (e.g., 5a, 5b, 5g) were significantly more water-soluble than CB30865 (636 μM for 5a at pH 6 and 992 μM for 5g at pH 6). In addition, some of them were up to 6-fold more cytotoxic than CB30865 (e.g., for 5a, W1L2 IC50 = 0.49 ± 0.24 nM) and retained its novel biochemical characteristics.