A sonochemical approach to 4-substituted pyrrolo[1,2-α]quinoxalines via Cu-catalyzed N-arylation followed by Wang resin/air promoted oxidative cyclization strategy

被引：5

作者：

Chemboli, Raviteja ^{[1
]}

Mandava, Bhuvan Tej ^{[1
]}

Kodali, Unati Sai ^{[2
]}

Taneja, Amit Kumar ^{[3
]}

Mandava, Bhagya Tej ^{[4
]}

Chandana, Oruganti Sesha Sri ^{[5
]}

Sultana, Md. Shabana ^{[6
]}

Yarlagadda, Bharath ^{[7
]}

Prasad, K. R. S. ^{[1
]}

Rao, Mandava Venkata Basaveswara ^{[8
]}

Pal, Manojit ^{[9
]}

机构：

[1] Koneru Lakshmaiah Educ Fdn, Dept Chem, Guntur 522302, Andhra Pradesh, India

[2] Dr NTR Univ Hlth Sci, Dr Pinnamaneni Siddhartha Inst Med Sci & Res Fdn, Vijayawada, Andhra Pradesh, India

[3] Chaudhary Charan Singh Univ, Dept Chem, Meerut 250001, India

[4] NRI Acad Med Sci, Dept MBBS, Guntur 522503, Andhra Pradesh, India

[5] Aditya Engn Coll, Surampalem 533437, India

[6] RV Inst Technol, Dept Humanities & Basic Sci, Guntur 522212, Andhra Pradesh, India

[7] Hiray Pharm Solut Ltd, 1,Xinghua Third Rd, Jingmen, Hubei, Peoples R China

[8] Krishna Univ, Dept Chem, Rudravaram, Andhra Pradesh, India

[9] Univ Hyderabad Campus, Dr Reddys Inst Life Sci, Hyderabad 500046, India

来源：

TETRAHEDRON LETTERS | 2024年 / 136卷

关键词：

Pyrrolo[1,2-alpha]quinoxaline; Ultrasound; Wang resin; SIRT1; EFFICIENT SYNTHESIS; BIOLOGICAL EVALUATION; STRUCTURAL BASIS; BRONSTED ACID; SIRT1; DERIVATIVES; ACTIVATION; SIRTUINS; CLEAVAGE; CANCER;

D O I：

10.1016/j.tetlet.2024.154917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 4 -substituted pyrrolo[1,2-a]quinoxaline framework was explored for the identification of possible inhibitors of SIRT1. To access the target compounds a general and ultrasound assisted two-step approach was developed for the first time involving the Cu -catalyzed N-arylation followed by Wang resin/air promoted oxidative cyclization strategy. Thus, C-N coupling of 2-iodoanilines with pyrrole gave the 1-(2-aminophenyl)pyrrole derivatives in the first step which on C--N/C-C bond formation with aldehydes afforded the desired products. The second step proceeded in pure water under open air and recovery as well as reuse of the Wang resin catalyst was demonstrated. The methodology offers advantages such as shorter duration, use of eco-friendly energy and wider substrate scope. Further application of this sonochemical method was also demonstrated via Suzuki coupling of a bromo product. Some of the pyrrolo[1,2-a]quinoxalines showed encouraging (52-77 %) inhibition of SIRT1 in vitro (better than nicotinamide) and were identified as initial hits.

引用

页数：6