16064-08-7

Basic information

• Product Name: 6-Iodoquinazolin-4-one
• Synonyms: 6-Iodo-4(1H)-quinazolinone;6-Iodo-4-quinazolinol;6-Iodoquin;6-Iodo-4-quinazolinol 6-Iodo-4-quinazolinone;6-iodoquinazolin-4(3H)-one;4-Hydroxy-6-iodoquinazoline;6-Iodoquinazolin-4-one,95+;TIMTEC-BB SBB005376
• CAS NO: 16064-08-7
• Molecular Formula: C₈H₅IN₂O
• Molecular Weight: 272.04
• EINECS: 1308068-626-2
• Product Categories: Lapatinib;pharmacetical
• Mol File: 16064-08-7.mol
• Article Data: 48

Chemical Properties

• Melting Point: 271°C(lit.)
• Boiling Point: 401 ºC at 760 mmHg
• Flash Point: 196.3 ºC
• Appearance: /
• Density: 2.11 g/cm³
• Vapor Pressure: 1.22E-06mmHg at 25°C
• Refractive Index: 1.779
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 1.00±0.20(Predicted)
• CAS DataBase Reference: 6-Iodoquinazolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Iodoquinazolin-4-one(16064-08-7)
• EPA Substance Registry System: 6-Iodoquinazolin-4-one(16064-08-7)

Safety Data

• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 16064-08-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

6-Iodoquinazolin-4-one is an intermediate in the synthesis of Lapatinib (L175800).

InChI:InChI=1/C8H5IN2O/c9-5-1-2-7-6(3-5)8(12)11-4-10-7/h1-4H,(H,10,11,12)

Upstream product

• 77287-34-4 formamide 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 64392-62-7 formamidinium acetate 
• 3473-63-0 formamidine acetic acid 
• 149-73-5 trimethyl orthoformate 
• 32658-67-6 2-amino-5-iodoanthranilamide 
• 77317-55-6 methyl 2-amino-5-iodobenzoate 
• 107-31-3 Methyl formate 
• 122-51-0 orthoformic acid triethyl ester 
• 544423-71-4 ammonium 5-iodoanthranilate 
• 98556-31-1 4-chloro-6-iodoquinazoline 
• 107-21-1 ethylene glycol 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 98556-31-1 4-chloro-6-iodoquinazoline 
• 660399-53-1 tert-butyl 4-(6-iodo-4-oxoquinazolin-3-ylmethyl)benzoate 
• 152536-21-5 4-hydroxyquinazoline-6-carboxylic acid methyl ester 
• 206190-28-5 6-phenylquinazolin-4(3H)-one 
• 1432450-48-0 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(quinolin-5-yl)quinazolin-4-amine 
• 1432450-49-1 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(2-phenoxyphenyl)quinazolin-4-amine 
• 1432450-50-4 6-(benzo[b]thiophen-2-yl)-N-(3-chloro-4-((3-fluorobenzyl)-oxy)phenyl)quinazolin-4-amine 
• 1432450-51-5 4-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-quinazolin-6-yl)phenol 
• 1432450-52-6 5-(4-(((3-chloro-4-(3-fluorobenzyl)oxy)phenyl)amino)-quinazolin-6-yl)pyrimidine-2,4(1H,3H)-dione 
• 1432567-60-6 C₃₁H₂₇FN₄O₄S 

Relevant articles and documents

New Acetohydrazides Incorporating 2-Oxoindoline and 4-Oxoquinazoline: Synthesis and Evaluation of Cytotoxicity and Caspase Activation Activity

In our search for new small molecules activating procaspase-3, we have designed and synthesized a series of new acetohydrazides incorporating both 2-oxoindoline and 4-oxoquinazoline scaffolds. Biological evaluation showed that a number of these acetohydrazides were comparably or even more cytotoxic against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI?H23, lung cancer) in comparison to PAC-1, a first procaspase-3 activating compound, which was used as a positive control. One of those new compounds, 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N′-[(3Z)-5-methyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene]acetohydrazide activated the caspase-3 activity in U937 human lymphoma cells by 5-fold higher than the untreated control. Three of the new compounds significantly induced necrosis and apoptosis in U937 cells.

(E)-N'-Arylidene-2-(4-oxoquinazolin-4(3H)-yl) acetohydrazides: Synthesis and evaluation of antitumor cytotoxicity and caspase activation activity

In our search for novel small molecules activating procaspase-3, we have designed and synthesised a series of novel acetohydrazides incorporating quinazolin-4(3H)-ones (5, 6, 7). Biological evaluation revealed eight compounds with significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5t displayed cytotoxicity up to 5-fold more potent than 5-FU. Analysis of structure-activity relationships showed that the introduction of different substituents at C-6 position on the quinazolin-4(3H)-4-one moiety, such as 6-chloro or 6-methoxy potentially increased the cytotoxicity of the compounds. In term of caspase activation activity, several compounds were found to exhibit potent effects, (e.g. compounds 7 b, 5n, and 5l). Especially, compound 7 b activated caspases activity by almost 200% in comparison to that of PAC-1. Further docking simulation also revealed that this compound potentially is a potent allosteric inhibitor of procaspase-3.

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Novel (Z)-N'-(2-oxoindolin-3-ylidene)-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides and an anticancer composition comprising the same as an active ingredient

(Z)- N' - (2-oxoindolin -3 - ylidene) -2 - (4-oxoquinazolin -3 (4H) - yl) acetohydrazide and an anticancer composition containing the same as an active ingredient. , It will be described below. (Z)- N' - (2-oxoindoline -3 - ylidene) -2 - (4-oxazoline -3 (4H) - yl) acetohydrazide according to the present invention activates procacaspase -3 to promote the conversion to caspase -3, so that it can be used as a proliferation inhibitor for various cancer cells. The compound according to the present invention can be developed as an active ingredient of a potent anticancer agent.