Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus

Brahmbhatt, Keyur G.; Ahemad, Nafees; Sabde, Sudeep; Mitra, Debashis; Singh, Inder Pal; Bhutani, K. K.

doi:10.1016/j.bmcl.2010.06.052

Cited by 60 publications

(25 citation statements)

References 21 publications

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“…[24] Interestingly,m ethyl 1-formyl-9H-pyrido [3,4-b]indole-3-carboxylate (3)i sk nownt o display mild anti-HIV activity. [25] Bracher and Hildebrand achieved the first synthesis of naturally occurring KumujianC(7) [26] in 51 %y ield from the reaction of dimetalated b-carboline (6)w ith DMF as an electrophile (Scheme 4). [27] Kumujancinew as first synthesized by Ta kasu et al [28,29] through aPictet-Spengler condensation reaction of tryptamine (8)w ith ethyl glyoxalate, followed by acylationw ith acetyl chloride, which furnished THbC 9;s ubsequent DDQ-mediated oxidation led to the formation of a4 -oxocarboline intermediate (10).…”

Section: Synthesis Of 1-formyl-b-carbolinesmentioning

confidence: 99%

“…This modified approach shortenedt he reaction time for these two steps from 8days to < 2h in am ore-economical manner (l-tryptophan is cheaper than tryptamine).F urthermore, deprotectiono ft he acetal group (15)a fforded the 1-formyl-9Hpyrido[3,4-b]indole (7). On the other hand, treatment of THbC derivative 24 with KMnO 4 in DMF only caused the oxidation of the Cring of THbCa nd afforded the corresponding b-carboline-3-carboxylic acid derivative (25). Further esterification, Nalkylation,a nd demasking of the acetal group afforded the N9substituted derivatives (26).…”

Section: Synthesis Of 1-formyl-b-carbolinesmentioning

confidence: 99%

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1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

et al. 2017

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b-Carboline, ap rivileged scaffold in the alkaloid family,h as ab road spectrum of medicinal properties and is found in severalc ommercial drugs, such as tadalafil, cipargamin, anda becarnil. Owing to the immense pharmacological importance of b-carboline derivatives, their synthesis has been one of the frontier areas of research in recent years. In this context,1 (3)-formyl-9H-b-carbolines are promising "aldo-X" bifunctional building blocks (AXB3s) that offer alternate avenues for the diversity-oriented synthesis of b-carboline derivatives. This Focus Review is an assimilation of recent literature (2011)(2012)(2013)(2014)(2015)(2016)(2017) pertaining to the synthesis and applicationso f1 (3)-formyl-b-carbolines for the construction of b-carboline-tethered and -fused moleculara rchitectures. In addition, the medicinal potential of b-carboline derivatives has been highlighted.

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Section: Synthesis Of 1-formyl-b-carbolinesmentioning

confidence: 99%

Section: Synthesis Of 1-formyl-b-carbolinesmentioning

confidence: 99%

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

et al. 2017

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“…Since then, more than 60 compounds with the characteristic tetracyclic core have been isolated from many other species, principally from the Rutaceae and Simaroubaceae families, and recently from fungi [2]. These compounds exhibited a broad spectrum of biological properties, including antiviral [3][4][5], anticancer [6][7][8], antiparasitic [9][10][11], anti-inflammatory [12,13], antibacterial [14][15][16], and antifungal [17,18] activity. Notably, canthine-6-one alkaloids have received considerable attention owing to their high antimicrobial potencies.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Ester Derivatives of 10-Hydroxycanthin-6-one as Potential Antimicrobial Agents

et al. 2016

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Abstract:As part of our continuing research on canthin-6-one antimicrobial agents, a new series of ester derivatives of 10-hydroxycanthin-6-one were synthesized using a simple and effective synthetic route. The structure of each compound was characterized by NMR, ESI-MS, FT-IR, UV, and elemental analysis. The antimicrobial activity of these compounds against three phytopathogenic fungi (Alternaria solani, Fusarium graminearum, and Fusarium solani) and four bacteria (Bacillus cereus, Bacillus subtilis, Ralstonia solanacearum, and Pseudomonas syringae) were evaluated using the mycelium linear growth rate method and micro-broth dilution method, respectively. The structure-activity relationship is discussed. Of the tested compounds, 4 and 7s displayed significant antifungal activity against F. graminearum, with inhibition rates of 100% at a concentration of 50 µg/mL. Compounds 5, 7s, and 7t showed the best inhibitory activity against all the tested bacteria, with minimum inhibitory concentrations (MICs) between 3.91 and 31.25 µg/mL. Thus, 7s emerged as a promising lead compound for the development of novel canthine-6-one antimicrobial agents.

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“…Carbolines are an important class of naturally occurring compounds containing the β-carboline motif found in a number of biologically active molecules, and which have recently been shown to be active against Alzheimer’s disease [1–2], bacterial infection [3], inflammation [4–5], HIV and AIDS [6] and various forms of cancers [7–12]. The wide range of therapeutic applications of these molecules highlights the importance of carbolines as a synthetic target in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine

Baiget¹,

Llona‐Minguez²,

Lang³

et al. 2011

Beilstein J. Org. Chem.

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SummaryThe carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet–Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1-carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.

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Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus

Cited by 60 publications

References 21 publications

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

1(3)‐Formyl‐β‐carbolines: Potential Aldo‐X Precursors for the Synthesis of β‐Carboline‐Based Molecular Architectures

Synthesis and Evaluation of Ester Derivatives of 10-Hydroxycanthin-6-one as Potential Antimicrobial Agents

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine

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