Natural products as templates for bioactive compound libraries: synthesis of biaryl derivatives of (±)-vasicine

Abstract

A reliable and high-yielding procedure for preparation of 7-aryl and 7-heteroaryl derivatives of (+/-)-vasicine in two steps from the naturally occurring material is described. This protocol broadens the chemical space for selective modifications of the vasicine tricyclic structure, thereby making it a valuable starting point for the development of novel compound libraries with potentially beneficial biological profiles.

4‐(Azolylphenyl)‐phthalazin‐1‐amines: Novel Inhibitors of VEGF Receptors I and II

“…Thus, 1,4‐dichlorophthalazine ( 6 ) was allowed to react with an aniline to give the mono‐displaced adduct ( 7 , 69–95% yields) (17), which was then transformed to the desired final compound 9a–z using Suzuki coupling reaction under microwave irradiation in a 55–78% isolated yields (Scheme 1). Boronic derivatives 8a–f were prepared as described by us earlier (18). Twenty‐six compounds ( 9a–z , Table 1) were tested in vitro against isolated VEGFR‐2.…”

1‐(Azolyl)‐4‐(aryl)‐phthalazines: Novel Potent Inhibitors of VEGF Receptors I and II†

“…A series of 1‐[5‐(phenyl)‐1 H ‐azol‐3‐yl]‐4‐(aryl)phthalazines 3–28 (Scheme 1) were synthesized by a three‐step procedure as described in Scheme 1 (18) Thus, 1 was allowed to react with a hydrazine to give 2 (78–95% yields), which was then transformed to the desired final compounds 3–28 by a two‐step sequence including conversion to a respective aryl chloride and Suzuki reaction under microwave irradiation (Scheme 1; 19,20). Boronic derivatives a–j were prepared as described earlier (21).…”

Chemical constituents and biological activities of species of Justicia: a review

“…Lignans are the major components of the active extracts of the species of Justicia, exhibiting important pharmacological properties, such as antiviral, antitumoral, anti-inflamatory, and Jiménez et al, 2001;Wang et al, 2004;Woodman et al, 2005;Woodman & Malakul, 2009 Apigenin (3) Anti-inflammatory and antitumor Wahi et al, 1974;Sawatzky et al, 2006;Cai et al, 2011 Kaempferitrin (4) Antimicrobial, antiinflammatory, regulators of macrophages, and reduce the blood glucose level J. spicigera CHCl 3 Dominguez et al, 1990;Abdel-Ghani et al, 2001;Fang et al, 2005;Cazarolli et al, 2006 Vitexin (5) Anti-inflammatory and antinociceptive Wahi et al, 1974;Sridhar et al, 2006;Gorzalczany et al, 2011 Rev. Mehta et al, 1963;Ikram & Huq, 1966;Bhalla et al, 1982;Chakravarthy et al, 1982;Jindal et al, 1988;Ismail et al, 1998;Lorenz et al, 1999;Claeson et al, 2000;Shevyakov et al, 2006;Rachana et al, 2011 Vasicinone (10) Bronchodilator J. adhatoda EtOH Amin & Mehta, 1959;Mehta et al, 1963;Ikram & Huq, 1966;Bhalla et al, 1982;Chakravarthy et al, 1982;Ismail et al, 1998;Jindal et al, 1998;Lorenz et al, 1999;Rachana et al, 2011 Allantoin (11) Anti-inflammatory and anti-ulcer Fukamiya & Lee, 1986;…”