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α-Benzylidene-2,3-tetramethylene-3,4-dihydroquinazol-4-one is a complex organic compound with the molecular formula C18H19N3O. It is a derivative of quinazolinone, a heterocyclic compound with a fused benzene ring and a quinazoline ring. This specific compound features a benzylidene group (a carbonyl group attached to a benzene ring) at the α-position, a tetramethylene bridge (four methylene groups) between the quinazoline and the benzene rings, and a dihydro structure, indicating the presence of two hydrogen atoms in the molecule. It is known for its potential applications in medicinal chemistry, particularly as a precursor in the synthesis of various bioactive compounds. The compound's structure and properties make it a subject of interest for researchers exploring new drug candidates and chemical entities with potential therapeutic effects.

94271-23-5

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94271-23-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 94271-23-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,2,7 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 94271-23:
(7*9)+(6*4)+(5*2)+(4*7)+(3*1)+(2*2)+(1*3)=135
135 % 10 = 5
So 94271-23-5 is a valid CAS Registry Number.

94271-23-5Relevant academic research and scientific papers

Design, synthesis and evaluation of arylidene pyrrolo and pyrido fused quinazolones as antimicrobial agents

Nepali, Kunal,Ojha, Ritu,Singh, Aninder,Budhiraja, Abhishek,Bedi, Preet Mohinder Singh,Dhar, Kanaya Lal

, p. 522 - 528 (2013/07/26)

Keeping in view the potential of heterocyclic fused quinazolones and arylidene linked heterocycles , hybrid molecules of these functionalities were designed and synthesised. All the synthesised molecules were characterized by spectroscopic techniques and evaluated for antimicrobial activity against 2 Gram positive bacterial strains; Staphylococcus aureus (MTCC 96) and Bacillus subtilis (MTCC 2451), 3 Gram negative bacterial strains; Escherichia coli (MTCC 82), Pseudomonas aeruginosa (MTCC 2642) and Salmonella typhimurium (MTCC 1251) and 2 fungal strains; Saccharomyces cerevisiae (MTCC 2799) and Candida albicans (MTCC 3018). Among the synthesised molecules, arylidene pyrrolo fused quinazolones displayed significant antimicrobial activity in comparison to arylidene pyrido fused quinazolones. The influence of the electronic factors linked with the arylidene ring was also observed on the antimicrobial potential. Thus the present study highlights the potential of such hybrid molecules as a new class of antimicrobials.

Structure activity relationship of arylidene pyrrolo and pyrido [2,1-b] quinazolones as cytotoxic agents: Synthesis, SAR studies, biological evaluation and docking studies

Mangla, Veenu,Nepali, Kunal,Singh, Gagandip,Singh, Jagjeet,Guru, Santosh,Gupta, Manish Kumar,Mahajan, Priya,Saxena, Ajit Kumar,Dhar, Kanaya Lal

, p. 642 - 650 (2013/09/23)

Tubulin is the one of the most useful and strategic molecular targets for anticancer drugs. Agents that bind in Colchicine-binding site of tubulin include Phenstatin, Combretastatin A-4, Colchicine, Steganacin, Podophyllotoxin and certain other synthetic analogues of these compounds. Arylidene pyrollo and pyrido [2,1-b] quinazolones (isoindigatone and its synthetic analogues) have been earlier reported to be tubulin inhibitors evidenced by tubulin polymerization assay. The present study is an extension of the library of the isoindigatone and its synthetic analogues to generate the structure activity relationship. The study explores the role of the arylidene ring and also provides some intresting observations such as the placement of bicyclic ring such as naphylidene for potential activity. Some of the important interactions of KNH-3 and KNH-11 with the amino acid residues of active site of Tubulin have also been observed by molecular modeling.

New topoisomerases inhibitors: Synthesis of rutaecarpine derivatives and their inhibitory activity against topoisomerases

Kim, Seung Ill,Lee, Seung Ho,Lee, Eung-Seok,Lee, Chong-Soon,Jahng, Yurngdong

experimental part, p. 785 - 789 (2012/08/29)

A series of rutaecarpine derivatives were prepared by employing previously reported methods and their inhibitory activities against topoisomerase I and II were evaluated. Among them, strongly cytotoxic 10-bromorutaecarpine and 3-chlororutaecarpine showed strong inhibitory activities against topo I and II.

Reaction of 2,3-tetramethylen-3,4-dihydroquinazol-4-one and its derivatives with aromatic aldehydes and furfurol

Abdurazakov,Elmuradov,Turdibaev,Shakhidoyatov

experimental part, p. 402 - 408 (2010/02/17)

α-Aryliden-6H(nitro)- and 6,8-dibromo-2,3-tetramethylen-3,4- dihydroquinazol-4-ones were synthesized by condensation of 6H(nitro)- and 6,8-dibromo-2,3-tetramethylen-3,4-dihydroquinazol-4-ones with aromatic aldehydes, furfurol, and of α-formyl-2,3-tetramethylen-3,4- dihydroquinazol-4-one with benzaldehyde and 4-nitrobenzaldehyde in glacial acetic acid.

A facile synthesis of α,α′-bis(substituted-benzylidene)-cycloalkanones and substituted-benzylidene heteroaromatics: utility of NaOAc as a catalyst for aldol-type reaction

Motiur Rahman,Jeong, Byeong-Seon,Kim, Dong Hyeon,Park, Jung Ki,Lee, Eung Seok,Jahng, Yurngdong

, p. 2426 - 2431 (2007/10/03)

Utility of NaOAc in glacial HOAc as a catalyst for aldol-type condensation reactions was examined. Reactions of cycloalkanones and selected heteroaromatics with various aldehydes in the presence of NaOAc in glacial HOAc provided α,α′-bis(substituted-benzylidene)cycloalkanones and substituted-benzylidene heteroaromatics, respectively, in good yields.

Privileged structure-based quinazolinone natural product-templated libraries: Identification of novel tubulin polymerization inhibitors

Liu, Ji-Feng,Wilson, Christopher J.,Ye, Ping,Sprague, Kevin,Sargent, Katie,Si, Ying,Beletsky, Galina,Yohannes, Daniel,Ng, Shi-Chung

, p. 686 - 690 (2007/10/03)

A focused quinazolinone natural product-templated library was designed and synthesized. Compounds from this privileged structure-based library were identified as antimitotic agents acting through destabilization of tubulin polymerization. The results suggested that 2 could be a privileged substructure.

A simple synthesis of rutaecarpine

Lee, Seung Ho,Kim, Seung Ill,Park, Jae Gyu,Lee, Eung Seok,Jahng, Yurngdong

, p. 1555 - 1567 (2007/10/03)

Indoloquinazoline alkaloid rutaecarpine was efficiently synthesized by employing 9,10,11,12-tetrahydro-4H-pyrido[2,1-b]quinazoline-4,9-dione as a key intermediate, whose 9-carbonyl group was introduced by benzylidene formation, followed by ozonolysis.

New Reactions of Deoxyvasicinone. Part 4.

Dunn, A. D.,Kinnear, K. I.

, p. 53 - 57 (2007/10/02)

Analogues of deoxyvasicinone (1) in which the pyrrolo ring is substituted, enlarged, or attached to the a face of the quinazolone system were prepared and several reactions of these analogues with electrophilic reagents have been investigated.

Synthesis of Tetrahydropyridoquinazolin-10(H)-one Analogues

Jain, M. P.,Gupta, V. N.,Atal, C. K.,Nath, L. G. D.

, p. 983 - 984 (2007/10/02)

Tetrahydropyridoquinazolin-10(H)-one analogues (III) have been synthesised by the condensation of 1,2,3,4-tetrahydropyridoquinazolin-10(H)-one (I) with different aromatic as well as aliphatic aldehydes (II) and screened for their bronchodilatory and uterotonic activities.Their structures have been established by elemental analyses and spectral data.

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