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13906-09-7

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13906-09-7 Usage

Uses

2-Mercapto-4(3H)-quinazolinone was employed as a modifier for the carbon paste electrode, for voltammetric determination of mercury. It was used in the synthesis of 4-quinazolinone derivatives, inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase.

General Description

The FTIR and FT-Raman spectra of 2-mercapto-4(3H) quinazolinone has been studied. Alkylation of 2-mercapto-4(3H)-quinazolinone has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 13906-09-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,0 and 6 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 13906-09:
(7*1)+(6*3)+(5*9)+(4*0)+(3*6)+(2*0)+(1*9)=97
97 % 10 = 7
So 13906-09-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H6N2OS/c11-7-5-3-1-2-4-6(5)9-8(12)10-7/h1-4H,(H2,9,10,11,12)

13906-09-7 Well-known Company Product Price

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  • Aldrich

  • (158828)  2-Mercapto-4(3H)-quinazolinone  97%

  • 13906-09-7

  • 158828-10G

  • 1,503.45CNY

  • Detail

13906-09-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-sulfanylidene-1H-quinazolin-4-one

1.2 Other means of identification

Product number -
Other names 2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13906-09-7 SDS

13906-09-7Relevant articles and documents

NEW SYNTHESIS OF 2-THIOXOQUINAZOL-4-ONES

Yangibaev, S.,Yun, L. M.,Shakhidoyatov, Kh. M.

, p. 712 (1985)

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SYNTHESIS AND ALKYLATION OF 2-MERCAPTO-4-QUINAZOLONE AND THE FUNGICIDAL ACTIVITIES OF THE COMPOUNDS OBTAINED

Shakhadoyatov, Kh. M.,Yangibaev, S.,Yun, L. M.,Kadyrov, Ch. Sh.

, p. 106 - 111 (1982)

A convenient method of obtaining 2-mercapto-4-quinazolone has been developed and the alkylation of its ambidentate anions has been studied.It has been found that they exhibit a dual reactivity in alkylation reactions.It has been shown that alkylated 2-mercapto-4-quinazolones possess a moderate fungicidal activity.

Synthesis, Cytotoxic Activity Evaluation of Novel 1,2,3-Triazole Linked Quinazoline Derivatives

Song, Panpan,Cui, Fei,Li, Na,Xin, Jingchao,Ma, Qisheng,Meng, Xiangchuan,Wang, Chaojie,Cao, Qinpo,Gu, Yifei,Ke, Yu,Zhang, Qiurong,Liu, Hongmin

, p. 1633 - 1639 (2017)

A series of novel 1,2,3-triazole-quinazoline derivatives were synthesized in five steps starting from anthranilamide by conventional methods. All the title compounds 10a—10r were evaluated for cytotoxic activity against four human cancer cell lines (MGC-803, EC-109, MCF-7 and HGC-27) using MTT assay in vitro. Some of the synthesized compounds exhibited moderate to potent activity against tested cancer cell lines. Among them, compounds 10 h and 10q exhibited excellent growth inhibition against HGC-27 and compound 10 m also possessed excellent activity against MCF-7, with IC50 values less than 1 μmol/L. Especially, compound 10 h was more cytotoxic than 5-fluorouracil against all tested four human cancer cell lines.

2,4-Disubstituted quinazolines targeting breast cancer cells via EGFR-PI3K

Li, Er-dong,Lin, Qiao,Meng, Ya-qi,Zhang, Lu-ye,Song, Pan-pan,Li, Na,Xin, Jing-chao,Yang, Peng,Bao, Chong-nan,Zhang, Dan-qing,Zhang, Yang,Wang, Ji-kuan,Zhang, Qiu-rong,Liu, Hong-min

, p. 36 - 47 (2019)

A series of novel 2,4-disubstituted quinazolines were synthesized and evaluated for their anti-tumor activity against five human cancer cells (MDA-MB-231, MCF-7, PC-3, HGC-27 and MGC-803) using MTT assay. Among them, compound 9n showed the most potent cytotoxicity against breast cancer cells. Compound 9n also significantly inhibited the colony formation and migration of MDA-MB-231 and MCF-7 cells. Meanwhile, compound 9n induced cell cycle arrest at G1 phase and cell apoptosis, as well as increased accumulation of intracellular ROS. Furthermore, compound 9n exerted anti-tumor effects in vitro via decreasing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 9n markedly decreased p-EGFR and p-PI3K expression, which revealed that compound 9n targeted breast cancer cells via interfering with EGFR-PI3K signaling pathway. Molecular docking suggested that compound 9n could indeed bind into the active pocket of EGFR. All the findings suggest that compound 9n might be a valuable lead compound for anti-tumor agents targeting breast cancer cells.

An efficient ionic liquid mediated synthesis of substituted 5H[1,3]-thiazolo[2,3-b]quinazoline-3,5-(2H)-dione and 5H-thiazolo[2,3-b] quinazolin-5-one

Yadav, Ashok K.,Dhakad, Pankaj,Sharma, Gopi Ram

, p. 6061 - 6063 (2013)

A new, environmentally benign two-step synthesis of 5H[1,3]-thiazolo[2,3-b] quinazoline-3,5-(2H)-dione and 5H-thiazolo[2,3-b]quinazolin-5-one derivatives has been accomplished stepwise. The substituted 2-aminobenzoic acid upon condensation with thiourea in 1-butyl-3-methylimidazolium bromide at moderate temperature under nitrogen atmosphere yielded 2-thioxo-1H-4-quinazolinones. The resulting intermediate 2-thioxo-1H-4-quinazolinones, when reacted with 2-chloroethanoic acid/2-chloropropanal underwent cyclization to yield the desired product in excellent yields.

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Jian, Yanlin,Forbes, He Eun,Hulpia, Fabian,Risseeuw, Martijn D. P.,Caljon, Guy,Munier-Lehmann, Hélène,Boshoff, Helena I. M.,Van Calenbergh, Serge

, p. 440 - 457 (2021/01/14)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

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