155184-81-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-chloro-5-methyl-benzoic acid is used as a building block for the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as antibiotics, anti-inflammatory agents, and other medicinal compounds.
Used in Agricultural Industry:
In the agricultural sector, 2-Amino-4-chloro-5-methyl-benzoic acid is utilized as a precursor for the synthesis of agrochemicals. It can be incorporated into the development of pesticides, herbicides, and other crop protection products, contributing to enhanced crop yields and improved agricultural practices.
Used as a Reagent in Organic Chemistry:
2-Amino-4-chloro-5-methyl-benzoic acid also serves as a reagent in organic chemistry, enabling various chemical reactions to produce other compounds. Its presence in these reactions can lead to the formation of new molecules with diverse applications, further expanding the scope of its utility in the chemical industry.

Upstream product

• 96187-75-6 6-chloro-5-methylisatin 
• 289686-80-2 2-cyano-5-chloro-4-methylaniline 
• 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 
• 95-74-9 3-chloro-p-toluidine 
• 1204312-39-9 4-chloro-5-methyl-N-acetylanthranilic acid 
• 155184-79-5 N-(3-chloro-4-methyl-phenyl)-2-hydroxyimino-acetamide 
• 7745-89-3 3-chloro-4-methylaniline hydrochloride 

Downstream Products

• 860193-26-6 7-chloro-6-methyl-3H-quinazolin-4-one 
• 458533-69-2 methyl 2-amino-4-chloro-5-methylbenzoate 
• 458533-71-6 methyl 2-methoxyacetamido-4-chloro-5-methylbenzoate 
• 458533-73-8 2-methoxyacetamido-4-chloro-5-methyl N-methylbenzamide 
• 289686-85-7 2-acetoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 289686-86-8 2-acetoxymethyl-6-bromomethyl-7-chloro-3-methyl-3,4-dihydroquinazolin-4-one 
• 289687-02-1 tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-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 
• 289687-01-0 tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroxyquinazolin-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 
• 289686-87-9 tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289687-03-2 tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-4-oxo-3,4-dihydroxyquinazolin-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 

Relevant academic research and scientific papers

BENZAMIDE DERIVATIVE

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

QUINAZOLINEDIONE DERIVATIVE

The present invention relates to quinazolinedione 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.

Anti-quinazoline compounds

Dihydroquinazoline derivatives of the formula where R3is —(CH2)p—A where p is from 1 to 4 and A is a 5- or 6-membered N-containing heterocyclic ring attached via the N atom or A is —NA′A″ wherein A′ and A″ are the same or different and are each a C1-C4alkyl group or their pharmaceutically acceptable salts possessing anti-cancer activity.

FUSED-RING PYRIMIDIN-4(3H)-ONE DERIVATIVES, PROCESSES FOR THE PREPARATION AND USES THEREOF

AbstractNovel compounds of the following formula (I) and pharmacologically acceptable salt and esters thereof can modulate LXR function and as a result show excellent anti-arteriosclerotic and anti-inflammatory activity:wherein:A represents aryl or heteroaryl;R1, R2 and R3 are the same or different and each represents hydrogen, hydroxyl, nitro, cyano, amino, halogen, carboxy, carbamoyl, mercapto, alkyl, haloalkyl, alkylcarbonyloxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, N-(alkylcarbonyl)-N-(alkyl)amino, alkoxycarbonylamino, N-(alkoxycarbonyl)-N-(alkyl)amino, alkylsulfonylamino, N-(alkylsulfonyl)-N-(alkyl)amino, haloalkylsulfonylamino, N-(haloalkylsulfonyl)-N-(alkyl)amino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, or R1 and R2 together are alkylenedioxy;R4 and R5 are the same or different and each represents hydrogen, hydroxyl, amino, halogen, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl or alkylthio;X represents hydrogen, hydroxyl, halogen, alkoxy or haloalkoxy; andY represents an optionally substituted alkyl, cycloalkyl, heterocyclyl, aryl, cycloalkylalkyl, heterocyclylalkyl or aralkyl group.

Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid

N-[5-[N-(2-Amino-5-chloro-3,4-dihydro-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (6) and N-[5-[N-(5-chloro-3,4-dihydro-2-methyl-4-oxoquinazolin-6-yl)methylamino]-2- thenoyl]-L-glutamic acid (7), the first reported thiophene analogues of 5-chloro-5,8-dideazafolic acid, were synthesized and tested as inhibitors of tumor cell growth in culture. 4-Chloro-5-methylisatin (10) was converted stepwise to methyl 2-amino-5-methyl-6-chlorobenzoate (22) and 2-amino-5-chloro-3,4-dihydro-6-methyl-4-oxoquinazoline (19). Pivaloylation of the 2-amino group, followed by NBS bromination, condensation with di-tert-butyl N-(5-amino-2-thenoyl)-L-glutamate (28), and stepwise cleavage of the protecting groups with ammonia and TFA yielded 6. Treatment of 9 with acetic anhydride afforded 2,6-dimethyl-5-chlorobenz[1,3-d]oxazin-4-one (31), which on reaction with ammonia, NaOH was converted to 2,6-dimethyl-5-chloro-3,4-dihydroquinazolin-4-one (33). Bromination of 33, followed by condensation with 28 and ester cleavage with TFA, yielded 7. The IC50 of 6 and 7 against CCRF-CEM human leukemic lymphoblasts was 1.8±0.1 and 2.1±0.8 μM, respectively.

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.

Synthesis of 3,4-Dihydro-1,4-ethenonaphthalen-2(1H)-ones by Benzyne Cycloadditions.

As part of a project on the photochemistry of 3,4-dihydro-1,4-ethanonaphthalen-2(1H)-ones (benzobicyclooctanones), we were interested in preparing the model 9-ene precursors shown in Scheme 1.On the basis of previous work, it was envisaged that the