Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

Author(s)

Nishimura, V, Rodolfo H. ; dos Santos, Thiago ^[1] ; Murie, Valter E. ^[1] ; Furtado, Luciana C. ^[2] ; Costa-Lotufo, V, Leticia ; Clososki, Giuliano C. ^{[1, 3]}

Affiliation

^[1] Nishimura, Rodolfo H., V, Univ Sao Paulo, Nucleo Pesquisas Prod Nat & Sintet, Dept Ciencias BioMoleculares, Fac Ciencias Farmaceut Ribeirao Preto, Av Caf S-N, BR-14040903 Ribeirao Preto, SP - Brazil

^[2] V, Univ Sao Paulo, Inst Ciencias Biomed, Av Lineu Prestes 1524, BR-05508900 Sao Paulo, SP - Brazil

^[3] Nishimura, Rodolfo H., V, Univ Sao Paulo, Dept Quim, Fac Filosofia Ciencias & Letras Ribeirao Preto SP, Av Bandeirantes 3900, BR-14090901 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Beilstein Journal of Organic Chemistry; v. 17, p. 2968-2975, DEC 22 2021.
• Web of Science Citations: 0

Abstract

Microwave-mediated N-arylation of 4-chloroquinazolines in THF/H2O rapidly and efficiently afforded a library of novel 6-halo-2- phenyl-substituted 4-anilinoquinazolines. The methodology was compatible with numerous ortho-, meta-, and para-substituted N-methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties. (AU)

• FAPESP's process: 15/17177-6 - Integrative approach on the sustainable prospection of marine natural products: from diversity to anticancer compounds
• Grantee: Leticia Veras Costa Lotufo
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 17/18235-5 - Anticancer potential of isolated substances from Streptomyces SP. recovered from ascidian Euherdmania SP
• Grantee: Luciana Costa Furtado
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 15/21364-6 - Applicantion of Organometallic Reagents in the Directed Functionalization of Quinolines Aimming the Synthesis of Medicinal Interest Compounds
• Grantee: Valter Eduardo Murie
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 18/14150-8 - Selective aromatic functionalization: Methodological Studies and new applications in the synthesis of BIOATIVE compounds
• Grantee: Giuliano Cesar Clososki
• Support Opportunities: Regular Research Grants
• FAPESP's process: 20/08987-2 - Effect of histone deacetylase and proteasome inhibitors in Glioma models
• Grantee: Luciana Costa Furtado
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 15/01466-9 - Directed functionalization of quinazolines and quinazolinones aiming the synthesis of bioactive substances
• Grantee: Rodolfo Hideki Vicente Nishimura
• Support Opportunities: Scholarships in Brazil - Doctorate