Three-component, one-pot synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives under catalyst free conditions and evaluation of their anti-inflammatory activity

Bioorg Med Chem Lett. 2016 Feb 1;26(3):858-863. doi: 10.1016/j.bmcl.2015.12.078.

Yasodakrishna Sajja ¹, Hanmanth Reddy Vulupala ¹, Rajashaker Bantu ¹, Lingaiah Nagarapu ², Sathish Babu Vasamsetti ³, Srigiridhar Kotamraju ³, Jagadeesh Babu Nanubolu ⁴

Affiliations

1 Organic Chemistry Division-II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
2 Organic Chemistry Division-II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. Electronic address: lnagarapuiict@yahoo.com.
3 Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
4 Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

PMID: 26748696 DOI: 10.1016/j.bmcl.2015.12.078

Abstract

An efficient three-component protocol is described for the synthesis of benzo[6,7]cyclohepta[1,2-b]pyridine derivatives using β-chloroacroleins, 1,3-dicarbonyls and ammonium acetate under catalyst free conditions by using ethanol as reaction media. The mild reaction conditions, operational simplicity and high yields are the advantages of this protocol and the broad scope of this one-pot reaction makes this procedure promising for practical usages. All the final compounds were screened for anti-inflammatory activity. Among the compounds tested, the compounds 5a, 5b, 5c, 5d, 5f, and 5k exhibited significant inhibition of IL-1β and MCP-1 secretion as a measure of anti-inflammatory activity.

Keywords

Ammonium acetate; Anti-inflammatory activity; Benzosuberone; Catalyst free conditions; One-pot reaction; Vilsmeier Haack Arnold reaction.

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