Design, synthesis and  in-vitro  evaluation of novel tetrahydroquinoline carbamates as HIV-1 RT inhibitor and their antifungal activity

Chander, Subhash; Ashok, Penta; Zheng, Yong‐Tang; Wang, Ping; Raja, Krishnamohan S.; Taneja, Akash; Murugesan, Sankaranarayanan

doi:10.1016/j.bioorg.2015.12.005

Cited by 36 publications

(13 citation statements)

References 32 publications

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“…Intrigued by these recent discoveries, we report on a concept of nanosized Ni-catalyzed simultaneous formation of C–C and C–N bonds. We exemplarily applied this concept to the synthesis of 1,2,3,4-tetrahydroquinoline (THQ) and its derivatives, which can be widely applied in the synthesis of biologically active natural products, − pharmacologically relevant agents, − value-added or fine chemicals, , and important intermediates, ,− from 2-anmino benzyl alcohols and primary alcohols. Previously, the synthesis of the THQ was mainly achieved via reduction of quinolines or the individual formation of C–N − or C–C bonds. , …”

Section: Introductionmentioning

confidence: 99%

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Zhang

Zhu

et al. 2019

ACS Catal.

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Simultaneous formation of C–C/C–N bonds provides insight into the bottom-up synthesis of N-heterocycles. This work reports Ni0/Niδ+ synergistic catalysis on the surface of Ni nanoparticles for the highly efficient one-pot formation of C–C/C–N bonds, affording 1,2,3,4-tetrahydroquinoline and its derivatives from 2-amino benzyl alcohol and ethanol without any addition of liquor base or external hydrogen. Ni0/Niδ+ synergistic catalysis has been achieved by regulating the Ni particle size or activating the Ni surface with O2. In the dehydrogenation of −CH2–OH to −CHO, the formation of CC and CN bonds via concurrent cross-condensation, and the transformation of CC/CN to C–C/C–N via hydrogen transfer, ethanol dehydrogenation has been found to be the rate-determining step. Reducing the Ni particle size effectively increases the number of surface Niδ+ sites, which accelerates catalytic dehydrogenation through synergistic catalysis between surface Niδ+ and Ni0 sites. The number of surface Niδ+ sites can be further increased by appropriately activating the Ni surface with O2.

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Section: Introductionmentioning

confidence: 99%

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Zhang

Zhu

et al. 2019

ACS Catal.

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“…Novel phenylcarbamate derivatives with tetrahydroquinoline were designed as inhibitors of HIV-1 reverse transcriptase (RT) also showed antifungal activity against C. albicans and A. niger (Chander et al 2016). The most active derivative (27, Fig.…”

Section: Antifungal Activitymentioning

confidence: 99%

“…Using the ligand based drug design approach the 1-(4-chlorophenyl)-2-(3,4-dihydroquinolin-1(2H)-yl)ethyl phenylcarbamate derivatives were designed as inhibitors of HIV-1 RT (Chander et al 2016). The most active compounds 56 and 57 (Fig.…”

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confidence: 99%

Quinolines and Quinolones as Antibacterial, Antifungal, Anti-virulence, Antiviral and Anti-parasitic Agents

Šenerović

Opsenica

Morić

et al. 2019

Advances in Experimental Medicine and Biology

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Infective diseases have become health threat of a global proportion due to appearance and spread of microorganisms resistant to majority of therapeutics currently used for their treatment. Therefore, there is a constant need for development of new antimicrobial agents, as well as novel therapeutic strategies. Quinolines and quinolones, isolated from plants, animals, and microorganisms, have demonstrated numerous biological activities such as antimicrobial, insecticidal, antiinflammatory, antiplatelet, and antitumor. For more than two centuries quinoline/quinolone moiety has been used as a scaffold for drug development and even today it represents an inexhaustible inspiration for design and development of novel semi-synthetic or synthetic agents exhibiting broad spectrum of bioactivities. The structural diversity of synthetized compounds provides high and selective activity attained through different mechanisms of action, as well as low toxicity on human cells. This review describes quinoline and quinolone derivatives with antibacterial, antifungal, anti-virulent, antiviral, and anti-parasitic activities with the focus on the last 10 years literature.

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“…Central role of RT enzyme in the life cycle of HIV makes it an attractive target and it has been exploited clinically for reduction of viral load from serum [3]. NNRTIs are crucial component of the current anti-HIV therapy named Highly Active Anti Retroviral Therapy (HAART), due to their potent anti-viral activity, high specificity and low toxicity [4][5][6]. However, continuous emergence of drug resistance against clinically used NNRTIs compromises their usefulness [7].…”

Section: Introductionmentioning

confidence: 99%

Hit optimization studies of 3-hydroxy-indolin-2-one analogs as potential anti-HIV-1 agents

Chander

Tang

Ashok

et al. 2018

Bioorganic Chemistry

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In the current study, twenty-two compounds based upon 3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one nucleus were designed, synthesized and in vitro evaluated for HIV-1 RT inhibition and anti-HIV-1 activity. Compounds 3d, 5c and 5e demonstrated encouraging potency against RT enzyme as well as HIV-1 in low micromolar to nanomolar concentration with good to excellent safety index. Structure activity relationship studies revealed that halogens such as bromo or chloro at 5th the position of oxindole ring remarkably enhanced the potency against RT. Moreover, methoxy or chloro groups at the ortho position of phenyl ring also significantly favored RT inhibition activity. Seven compounds (3b, 3c, 3d, 3e, 5b, 5c and 5e) with better anti-HIV-1 potency were tested against the mutant HIV-1 strain The putative binding mode, as well as interaction patterns of the best active compound 5c with wild HIV-1 RT were studied via docking studies.

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Design, synthesis and in-vitro evaluation of novel tetrahydroquinoline carbamates as HIV-1 RT inhibitor and their antifungal activity

Cited by 36 publications

References 32 publications

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Quinolines and Quinolones as Antibacterial, Antifungal, Anti-virulence, Antiviral and Anti-parasitic Agents

Hit optimization studies of 3-hydroxy-indolin-2-one analogs as potential anti-HIV-1 agents

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Design, synthesis and in-vitro evaluation of novel tetrahydroquinoline carbamates as HIV-1 RT inhibitor and their antifungal activity

Cited by 36 publications

References 32 publications

Ni0/Niδ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Ni0/Niδ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Quinolines and Quinolones as Antibacterial, Antifungal, Anti-virulence, Antiviral and Anti-parasitic Agents

Hit optimization studies of 3-hydroxy-indolin-2-one analogs as potential anti-HIV-1 agents

Contact Info

Product

Resources

About

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds

Ni⁰/Ni^δ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds