Synthesis and biological evaluation of novel 5(H)-phenanthridin-6-ones, 5(H)-phenanthridin-6-one diketo acid, and polycyclic aromatic diketo acid analogs as new HIV-1 integrase inhibitors

Patil, Shivaputra A.; Kamath, Shantaram; Sanchez, Tino W.; Neamati, Nouri; Schinazi, Raymond F.; Buolamwini, John K.

doi:10.1016/j.bmc.2006.11.026

Cited by 100 publications

(66 citation statements)

References 28 publications

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“…Substituting the carboxylic acid in diketo acids with phosphonic acid led to a shift in selectivity of the resulting compounds toward inhibition of IN catalytic steps. 40 Compound 1 inhibited 3 0 -processing and ST with IC 50 values of 3.7 and 0.2 mM, respectively; whereas the corresponding phosphonic acid isostere compound 2 inhibited 3 0 -processing and ST with IC 50 values of 333 and 20 mM, respectively (Fig. 4).…”

Section: A Diketo Phosphonic Acidmentioning

confidence: 96%

“…9). 50 The structures with the phenanthridinone scaffold exhibited only a weak inhibitory activity. Incorporating the diketo acid functionality conferred an improvement in inhibitory potency.…”

Section: Aryl Diketo Acid Derivativesmentioning

confidence: 99%

“…22 It belongs to the class of pyrimidinone carboxamides that are similar to the naphthyridine carboxamides. Raltegravir shows an excellent in vitro IN inhibitory profile, with an in vitro IC 50 value of 2-7 nM against ST and CIC 95 5 31 nM in the presence of serum (Table II). It is also active against various viral strains that are resistant to other classes of antiretroviral agents.…”

Section: Hiv-1 Integrase Inhibitors: 2007--2008 Update K 893mentioning

confidence: 99%

“…Despite good antiviral activity (IC 50 value of 20 nM for ST inhibition), S-1360 failed in clinical trials due to a lack of efficacy. It turned out that the diketo acid moiety, important for IN inhibition, was also a good substrate for the aldo-keto reductase.…”

Section: Introductionmentioning

confidence: 99%

“…They show potent inhibition of the ST reaction with a good antiviral potency (Table I). 18,19 In fact, these compounds 50 5 Concentration that results in 50% inhibition of integrase activity.…”

Section: Introductionmentioning

confidence: 99%

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HIV-1 integrase inhibitors: 2007-2008 update

et al. 2010

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In recent years, HIV-1 integrase (IN) has become an attractive target for designing antiretroviral agents. The first IN inhibitor approved for clinical use, raltegravir, has validated the pharmacological viability of IN inhibitors and signals the advent of a new generation of antiretroviral drugs. The development of raltegravir and other successful lead IN inhibitors has also influenced the IN inhibitor design strategy. This has led to the identification of several potent inhibitors in these last two years. Further, an increased understanding of IN structural biology has opened up novel approaches to inhibiting IN, such as targeting its multimerization or interaction with cellular cofactors. This review covers recent developments in the field of IN inhibitor design from 2007 to 2008.

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Section: A Diketo Phosphonic Acidmentioning

confidence: 96%

Section: Aryl Diketo Acid Derivativesmentioning

confidence: 99%

Section: Hiv-1 Integrase Inhibitors: 2007--2008 Update K 893mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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HIV-1 integrase inhibitors: 2007-2008 update

et al. 2010

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Computer‐Aided Techniques in Design of HIV‐1 Integrase Inhibitors

et al. 2011

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(Hetero)Aryl CH Amination via Organic Electrochemistry

Shah¹,

Ngai²

2022

Handbook of CH-Functionalization

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Aromatic amines are essential compounds found in various natural products, drugs, and materials. Their widespread presence has motivated scientists worldwide to explore new avenues for the development of aromatic CN bond formation methodologies. Since the turn of the century, there has been a growing impetus to develop sustainable molecular syntheses. Having been recognized as an effective tool to control the redox events and flow of electrons between reactive species, organic electrocatalysis has been revived after being somewhat dormant for decades in industry and academia. This article provides an overview of electrocatalyzed aromatic CN bond formation reactions, which involve dehydrogenative coupling between aromatic CH bonds and amines through electrocatalysis. We present mechanistic insights and the scope of the methodology in terms of various substrates. We also have provided an outlook for future synthetic applications and different technologies that can merge with electrosynthesis.

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Synthesis and biological evaluation of novel 5(H)-phenanthridin-6-ones, 5(H)-phenanthridin-6-one diketo acid, and polycyclic aromatic diketo acid analogs as new HIV-1 integrase inhibitors

Cited by 100 publications

References 28 publications

HIV-1 integrase inhibitors: 2007-2008 update

HIV-1 integrase inhibitors: 2007-2008 update

Computer‐Aided Techniques in Design of HIV‐1 Integrase Inhibitors

(Hetero)Aryl CH Amination via Organic Electrochemistry

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