Synthesis of Novel Pyrimido[4,5-b]quinolin-4-ones with Potential Antitumor Activity

Abstract

in Wiley Online Library (wileyonlinelibrary.com). The 5,6,7,8,9,quinolines 4,5a-d and their oxidized forms 6,7a-d were obtained from the reaction of 6-amino-2-(methylthio)pyrimidin-4(3H)-one 2 or 6-amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one 3 and a,b-unsaturated ketones 1a-d using BF 3 .OEt 2 as catalyst and p-chloranil as oxidizing agent. Some of the new compounds were evaluated in the US National Cancer Institute (NCI), where compound 5a presented remarkable activity against 46 cancer cell lines, with the most important GI 50 values ranging from 0.72 to 18.4 mM from in vitro assays.

Domino synthesis of functionalized 1,6-naphthyridines and their in vitro anti-inflammatory and anti-oxidant efficacies

“…2,3 These pyridine structures are the most significant because of their wide spectrum of promising biological activities such as anticonvulsants, 4 anti-inflammatory, 5 antimitotic, 6 agents antioxidant, 7,8 anticancer, 9,10 and antimicrobial activities. 11 Similarly, 1,6-naphthyridines [12][13][14][15][16][17] have established significant attention due to their broad range of bioactivities [18][19][20][21][22][23][24] such as antimicrobial, 25 anti-analgesic, 26 antifungal, 27,28 anticancer, [29][30][31] antioxidant, 31 anti-inflammatory, [27][28][29]32 antiarrhythmic, 33 antitumor 34 , anti HSV-1 35 anti-HIV 36,37 activities and act as inhibitors of acetylcholinesteras. 38 Structures of few previously reported biologically active 1,6-naphyridines (A-G) are shown in Figure 1.…”

An Efficient Protocol for the Synthesis of Pyrido[2,3‐d]pyrimidines in Glycerol–Water Medium: Assessment by Green Chemistry Metrics

“…The expansion of clean and efficient synthetic strategies for the design of pharmacologically important nitrogen containing heterocycles and their fused derivatives is a significant aspect of medicinal and organic chemistry . From last two decades, a great deal of consideration has been intended for synthesis of pyrido[2,3‐ d ]pyrimidine derivatives due to their attractive biological and pharmacological properties such as antibacterial, antimicrobial, analgesic, anti‐inflammatory, antitumor, cardiotonic, antifungal, antihypertensive, and calcium channel antagonists . Consequently, a number of synthetic approaches have been reported for the preparation of pyrido[2,3‐ d ]pyrimidine derivatives .…”

Sodium‐Hydroxide‐Mediated Synthesis of Highly Functionalized [1,6]‐Naphthyridines in a One‐Pot Pseudo Five‐Component Reaction

“…1,6‐Naphthyridine derivatives, nitrogen heterocycles containing two pyridine rings, are widely distributed in nature,4 and they are considered to be “privileged structures” in drug discovery. These compounds show a wide range of pharmacological activities such as antitumor,5a antimicrobial,5b allosteric,5c and antiproliferative activities 5d. In addition, functionalized 1,6‐naphthyridines are well‐known inhibitors of human cytomegalovirus6a and HIV‐1 integrase,6b and are selective antagonists of 5‐HT4 receptors 6c.…”