116010-06-1

Basic information

• Product Name: N-Acetyl 2-bromo-5-chloro-4-methylaniline
• Synonyms: N-Acetyl 2-bromo-5-chloro-4-methylaniline;N-(2-Bromo-5-chloro-4-methylphenyl)acetamide
• CAS NO: 116010-06-1
• Molecular Formula: C₉H₉BrClNO
• Molecular Weight: 263
• Mol File: 116010-06-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Acetyl 2-bromo-5-chloro-4-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl 2-bromo-5-chloro-4-methylaniline(116010-06-1)
• EPA Substance Registry System: N-Acetyl 2-bromo-5-chloro-4-methylaniline(116010-06-1)

Safety Data

• Hazardous Substances Data: 116010-06-1(Hazardous Substances Data)

Usage

General Description

N-Acetyl 2-bromo-5-chloro-4-methylaniline is a compound consisting of an acetyl group, a bromine atom, a chlorine atom, and a methyl group attached to a 4-methylaniline molecule. It is commonly used in the pharmaceutical and chemical industries as an intermediate for the synthesis of various organic compounds. This chemical has the potential to be used in the development of new drugs, as well as in the production of dyes and pigments. Its unique structure and properties make it a versatile building block for creating a wide range of molecules with different functions and applications. However, it is important to handle this compound with caution, as it may have hazardous properties and should be used in a controlled environment by trained professionals.

Upstream product

• 95-74-9 3-chloro-p-toluidine 
• 7149-79-3 N-(3-chloro-4-methylphenyl)acetamide 

Downstream Products

• 1204312-39-9 4-chloro-5-methyl-N-acetylanthranilic acid 
• 108485-03-6 (2-bromo-5-chloro-4-methyl-anilino)-methanesulfonic acid ; sodium-salt 
• 289687-06-5 tert-butyl 4-[N-[7-chloro-4-oxo-2-piperidin-1-ylmethyl-3-piperidinocarbonylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 1026405-52-6 4-{[7-chloro-4-oxo-3-(2-oxo-2-piperidin-1-yl-ethyl)-2-piperidin-1-ylmethyl-3,4-dihydro-quinazolin-6-ylmethyl]-prop-2-ynyl-amino}-benzoic acid 
• 289687-05-4 tert-butyl 4-[N-[7-chloro-3-diethylcarbamoylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 1027938-29-9 4-[(7-chloro-3-diethylcarbamoylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoic acid 
• 289687-07-6 tert-butyl 4-[N-[7-chloro-3-methoxycarbonylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-98-2 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 
• 1026592-71-1 4-[(7-chloro-3-methoxycarbonylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoic acid 
• 289687-04-3 tert-butyl 4-[N-[7-chloro-2-(piperidin-1-yl)methyl-4-oxo-3,4-dihydroxyquinazolin-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 
• 289686-93-7 tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 

Relevant articles and documents

BENZAMIDE DERIVATIVE

The present invention relates to benzamide derivatives represented by formula (I) or pharmaceutically acceptable salts thereof.

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.