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在无催化剂条件下三组分一锅法合成苯并[6,7]环庚并[1,2-b]吡啶衍生物及其抗炎活性评价

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.

作者信息

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

机构信息

Organic Chemistry Division-II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

Organic Chemistry Division-II (CPC), CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

出版信息

Bioorg Med Chem Lett. 2016 Feb 1;26(3):858-863. doi: 10.1016/j.bmcl.2015.12.078. Epub 2015 Dec 23.

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.

摘要

描述了一种高效的三组分反应体系,在无催化剂条件下,以乙醇为反应介质,使用β-氯代丙烯醛、1,3-二羰基化合物和乙酸铵合成苯并[6,7]环庚并[1,2-b]吡啶衍生物。该反应体系具有反应条件温和、操作简便、产率高的优点,且该一锅法反应的适用范围广泛,使其在实际应用中具有前景。对所有最终化合物进行了抗炎活性筛选。在所测试的化合物中,化合物5a、5b、5c、5d、5f和5k表现出对IL-1β和MCP-1分泌的显著抑制,以此作为抗炎活性的指标。

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