289686-86-8

Basic information

• Product Name: (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate
• Synonyms: (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate
• CAS NO: 289686-86-8
• Molecular Formula: C₁₃H₁₂BrClN₂O₃
• Molecular Weight: 359.60298
• Mol File: 289686-86-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate(289686-86-8)
• EPA Substance Registry System: (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate(289686-86-8)

Safety Data

• Hazardous Substances Data: 289686-86-8(Hazardous Substances Data)

Usage

Description

(6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate is a chemical compound with the molecular formula C15H16BrClN2O3, derived from quinazolin-4(3H)-one. It is utilized in pharmaceutical research and development due to its unique structure and properties, which hold potential for the treatment of various diseases and conditions.

Uses

Used in Pharmaceutical Research and Development:
(6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate is used as a compound in pharmaceutical research and development for its potential applications in treating various diseases and conditions, including cancer and neurodegenerative disorders. Its unique structure and properties make it a valuable tool in the development of new drugs and therapies.
Used in the Treatment of Cancer:
In the field of oncology, (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate is used as a potential therapeutic agent for cancer treatment. Its specific mechanisms of action and interactions with biological targets are under investigation to determine its efficacy and safety in combating cancer cells.
Used in the Treatment of Neurodegenerative Disorders:
(6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate is also being explored for its potential use in the treatment of neurodegenerative disorders. Its unique properties may offer new avenues for therapeutic intervention in conditions such as Alzheimer's, Parkinson's, and other related diseases.
Used in Drug Design and Synthesis:
In the chemical and pharmaceutical industries, (6-(broMoMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)Methyl acetate is used as a key intermediate in the design and synthesis of new drugs. Its structural features make it a promising candidate for the development of novel therapeutic agents with improved efficacy and selectivity.

Upstream product

• 289686-85-7 2-acetoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 7149-79-3 N-(3-chloro-4-methylphenyl)acetamide 
• 102170-52-5 2-bromo-5-chloro-4-methylaniline 
• 116010-06-1 N-(2-bromo-5-chloro-4-methylphenyl)acetamide 
• 155184-81-9 2-amino-5-methyl-4-chlorobenzoic acid 
• 95-74-9 3-chloro-p-toluidine 
• 289686-80-2 2-cyano-5-chloro-4-methylaniline 
• 458533-69-2 methyl 2-amino-4-chloro-5-methylbenzoate 
• 458533-67-0 7-chloro-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 458533-77-2 2-hydroxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 458533-75-0 2-methoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 289686-83-5 7-chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one 
• 458533-71-6 methyl 2-methoxyacetamido-4-chloro-5-methylbenzoate 
• 458533-73-8 2-methoxyacetamido-4-chloro-5-methyl N-methylbenzamide 

Downstream Products

• 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 
• 289686-89-1 tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-91-5 tert-butyl4-[N-[2-diethylaminomethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-93-7 tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-94-8 tert-butyl 4-[N-[7-chloro-3-methyl-2-pyrrolidinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-90-4 tert-butyl 4-[N-[7-chloro-3-methyl-2-(4-methylpiperazin-1-ylmethyl)-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-92-6 tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-99-3 tert-butyl 4-[N-[7-chloro-3-methyl-2-(4-hydroxypiperidin-1-ylmethyl)-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-95-9 tert-butyl 4-[N-[7-chloro-3-methyl-2-(4-ethyl-piperazin-1-ylmethyl)-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-96-0 tert-butyl 4-[N-[7-chloro-3-methyl-2-(methyl-L-prolin-1-ylmethyl)-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 

Relevant articles and documents

Analogues of 4-[(7-Bromo-2-methyl-4-oxo-3 H -quinazolin-6-yl)methylprop-2- ynylamino]- N -(3-pyridylmethyl)benzamide (CB-30865) as potent inhibitors of nicotinamide phosphoribosyltransferase (Nampt)

We have shown previously that the target of the potent cytotoxic agent 4-[(7-bromo-2-methyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino] -N-(3-pyridylmethyl)benzamide (CB38065, 1) is nicotinamide phosphoribosyltransferase (Nampt). With its cellular target known we sought to optimize the biochemical and cellular Nampt activity of 1 as well as its cytotoxicity. It was found that a 3-pyridylmethylamide substituent in the A region was critical to cellular Nampt activity and cytotoxicity, although other aromatic substitution did yield compounds with submicromolar enzymatic inhibition. Small unsaturated groups worked best in the D-region of the molecule, with 3,3-dimethylallyl providing optimal potency. The E region required a quinazolin-4-one or 1,2,3-benzotriazin-4-one group for activity, and many substituents were tolerated at C2 of the quinazolin-4-one. The best compounds showed subnanomolar inhibition of Nampt and low nanomolar cytotoxicity in cellular assays.

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.