112888-43-4

Basic information

• Product Name: 6-Bromomethyl-3,4-dihydro-2-methyl-quinazolin-4-one
• Synonyms: 6-(BROMOMETHYL)-2-METHYL-4(1H)-QUINAZOLINONE;6-BROMOMETHYL-3,4-DIHYDRO-2-METHYL QUINAZOLIN-4-ONE;4,6-(Bromomethyl)-2-Methy Quinazolinone;6-(Bromomethyl)-2-methyl-4(3H)-quinazolinone;6-Bromomethyl-3,4-dihydro-2-methylquinazoline-4-one;6-Bromomethyl-3,4-dihydro-2-methyl-quizolin-4-one;4(3H)-Quinazolinone,6-(bromomethyl)-2-methyl-
• CAS NO: 112888-43-4
• Molecular Formula: C₁₀H₉BrN₂O
• Molecular Weight: 253.1
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Raltitrexed
• Mol File: 112888-43-4.mol

Chemical Properties

• Melting Point: >330 °C(Solv: chloroform (67-66-3))
• Boiling Point: 399.387 °C at 760 mmHg
• Flash Point: 195.342 °C
• Appearance: /
• Density: 1.634 g/cm³
• Vapor Pressure: 1.37E-06mmHg at 25°C
• Refractive Index: 1.669
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.21±0.20(Predicted)
• CAS DataBase Reference: 6-Bromomethyl-3,4-dihydro-2-methyl-quinazolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromomethyl-3,4-dihydro-2-methyl-quinazolin-4-one(112888-43-4)
• EPA Substance Registry System: 6-Bromomethyl-3,4-dihydro-2-methyl-quinazolin-4-one(112888-43-4)

Safety Data

• Hazardous Substances Data: 112888-43-4(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

Raltitrexed intermediate

InChI:InChI=1/C10H9BrN2O/c1-6-12-9-3-2-7(5-11)4-8(9)10(14)13-6/h2-4H,5H2,1H3,(H,12,13,14)

Upstream product

• 18731-19-6 3,4-dihydro-2,6-dimethyl-4-oxoquinazoline 
• 128-08-5 N-Bromosuccinimide 
• 7471-58-1 quinazolin-2-one 
• 99-04-7 m-Toluic acid 
• 72755-11-4 N-methoxy-3-methylbenzamide 
• 1082727-34-1 3,4 dihydro-2,6 dimethylquinazolin 
• 67081-68-9 2-acetamido-5-methylbenzoic acid 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 62175-49-9 2-methyl-6-methyl-4H-3,1-benzoxazin-4-one 

Downstream Products

• 112889-00-6 methyl p-[ N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-ethylamino]-o-nitrobenzoate 
• 133446-87-4 4-(2-Methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethoxy)-benzoic acid methyl ester 
• 161879-11-4 tert-butyl 4--N-ethylamino>benzoate 
• 172793-46-3 tert-butyl 4--N-prop-2-ynylamino>-2-fluorobenzoate 
• 173951-86-5 4-{4-[(2-Methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester 
• 130206-44-9 {4-[(2-Methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-2-trifluoromethyl-benzenesulfonylamino}-acetic acid methyl ester 
• 130206-42-7 6-{[(4-Benzenesulfonyl-phenyl)-prop-2-ynyl-amino]-methyl}-2-methyl-3H-quinazolin-4-one 

Relevant articles and documents

Synthesis of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone and their cytotoxic activity

A new series of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone were synthesized via four steps starting from 2-amino-5-methyl-benzoic acid and initially screened against A-549 (human non-small cell

Synthesis, Cytotoxic, and Antibacterial Evaluation of Quinazolinone Derivatives with Substituted Amino Moiety

A series of novel quinazolinone derivatives containing a substituted amino moiety were synthesized, evaluated for their cytotoxic and antibacterial activities. The results of MTT assay showed that all synthesized target compounds 5A?–?5O showed potent cytotoxicity against SGC-7901 (IC50, 0.72?–?1.41?μm). Moreover, the compounds 5D, 5I, and 5K showed better selectivity as compared with positive controls pemetrexed and MTX due to weak cytotoxicity against normal tissue cell line HUVSMC. Among synthesized compounds, the compounds 5E, 5J, 5L, and 5N showed broad-spectrum cytotoxic activities against at least four cancer cell lines at a micromolar level. The results of antibacteria evaluation revealed that all synthesized compounds showed good to moderate antibacterial activities against Gram-negative bacteria Escherichia coli. Among them, the MIC values of the compounds 5C, 5F, and 5M were 0.31?μg/mL.

Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains

A series of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains were synthesized and tested for their in vitro antitumor activity against human myelogenous leukemia K562 cells. Among them, (3,4-dihydro-2-methyl-4- oxoquinazolin-6-yl)methyl 4-(4-fluorophenyl)piperazine-1-carbodithioate 8q exhibited significant inhibitory activity against K562 cells with IC 50 value of 0.5 μM.

Cp?CoIII-catalyzed formal [4+2] cycloaddition of benzamides to afford quinazolinone derivatives

A Cp?CoIII-catalyzed arene C-H bond amidation/annulation of benzamides was developed to afford quinazolinone derivatives in one-pot with high yields and broad substrate scope. This method could be applied to the synthesis of quinazolinone drugs and late-stage modification of natural products.

Folic-acid antagonist for treating intestinal bacterial infection, preparation and application thereof

The invention relates to a folic-acid antagonist for treating intestinal bacterial infection, preparation and an application thereof. The folic-acid antagonist is a compound as shown in Formula I or asalt of the compound as shown in Formula I (the Formula

New enzymes and prodrugs for ADEPT

The present invention relates to nucleic acid molecules encoding mutant human carboxypeptidase A enzymes, and encoding conjugates of targeting molecules and mutant human carboxypeptidase A enzymes. The invention further relates to vectors and cell lines containing such nucleic acid molecules.

Anti-tumour agents

A quinazoline of the formula: STR1 wherein R1 is alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, aryl, aryloxy, arylalkyl, halogeno, hydroxy, mercapto, pyridylthio, pyrimidinylthio, or substituted alkyl or alkoxy; wherein R2 is hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl or alkanoyl; wherein Ar is phenylene, naphthylene or heterocyclene which is unsubstituted or bears one or more substituents and wherein R3 is such that R3 --NH2 is an amino acid; or a pharmaceutically-acceptable salt or ester thereof. The compounds possess anti-tumour activity.

Quinazoline antifolate thymidylate synthase inhibitors: Alkyl, substituted alkyl, and aryl substituents in the C2 position

Modification of the potent thymidylate synthase (TS) inhibitor N-[4-[N-[(2-amino-3,4-dihydro-4-oxo-6-quinazolinyl)methyl]-N-prop-2-yn ylamino]benzoyl]-L-glutamic acid (1a) has led to the synthesis of quinazoline antifolates bearing alkyl, substituted alkyl, and aryl substituents at C2. In general the synthetic route involved the coupling of the appropriate diethyl N-[4-(alkylamino)benzoyl]-L-glutamate with a C2-substituted 6-(bromo-methyl)-3,4-dihydro-4-oxoquinazoline followed by deprotection using mild alkali. Good enzyme inhibition and cytotoxicity were found with compounds containing small nonpolar groups in the C2 position with the 2-desamino-2-methyl analogue 3a being the most potent. Larger C2 substituents were tolerated by the enzyme, but cytotoxicity was reduced. Highly potent series were followed up by the synthesis of a number of analogues in which the N10 substituent was varied. In this manner a number of interesting TS inhibitors have been prepared. Although none of these was more potent than 1a against the isolated enzyme, over half of the compounds prepared were more potent as cytotoxic agents against L1210 cells in culture. The potential of such compounds as useful antitumor agents was further enhanced by the finding that the improved aqueous solubilities of compounds such as 3a over 1a were reflected in vivo in that 3a was at least 5 times less toxic to mice than 1a.

Folate analogues. 32. Synthesis and biological evaluation of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid and related compounds

The chemical synthesis of three close analogues (2-4) of N10-propargyl-5,8-dideazafolate (PDDF) is described. The quinazoline ring of 2 and 4 was constructed from the pivotal intermediate 9 in a novel and unambiguous manner during the final ste