Synthesis of indole-2-carbaldehydes, 2-(2-aminoethyl)- and 2-(2-aminopropyl)-indoles

Bhat, Gulzar Ahmad; Siddappa, S.

doi:10.1039/j39710000178

Cited by 6 publications

(4 citation statements)

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“…Compound 25 (100 mg, 0.56 mmol) and MnO 2 (490 mg, 5.6 mmol) in EtOAc (5 mL) were heated to reflux for 24 h. The mixture was filtered over Celite, and the filtrate was concentrated in vacuo and purified by chromatography (0% to 10% EtOAc/hexanes) to yield a pale-yellow powder (75 mg, 76%): mp 143–144 °C (lit. 61 140–141 °C). TLC R f 0.28 (20% EtOAc/hexanes).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity

et al. 2015

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Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2- and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity

et al. 2015

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“…General Method of Acylation of Diamines 7,11,[23][24][25][26] To Obtain Compounds 2,3,27,29,32,35-47, and 51-53. A solution of the aromatic acetyl chloride (1.0 mmol) in CH2C12 (5 mL) was added dropwise to a stirred solution of the diamine (0.9 mmol) in the same solvent (15 mL) in the presence of anhydrous potassium carbonate (1.0 mmol) at 0 °C.…”

Section: -[(L-pyrrolidinylmentioning

confidence: 99%

(1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: members of a novel class of very potent .kappa. opioid analgesics

Vecchietti¹,

Clarke²,

Colle³

et al. 1991

J. Med. Chem.

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The synthesis and structure-activity relationship (SAR) of a novel class of kappa opioid analgesics, 1-(aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines and (aminomethyl)-N-(arylacetyl)-4,5,6,7-tetrahydrothienopyridines+ ++, are described. These compounds, formally derived by the condensation of a benzene or thiophene ring on the piperidine nucleus of the recently described compounds 1, are from 3 to 7 times more potent as antinociceptive agents and with a longer duration of action than the original lead compounds. A similar N2-C1-C9-N10 pharmacophore torsional angle of approximately 60 degrees was also found for this class of compounds by using X-ray and 1H NMR analyses. The same absolute configuration (S) at the chiral center of the active (-) enantiomers was determined by X-ray crystallographic analysis. A varied degree of kappa receptor selectivity was a feature of this novel class of antinociceptive agents (mu/kappa ratio from 44 to 950 according to the nature of the basic moiety). SAR analysis indicated that the presence of electron-withdrawing and lipophilic substituents in para and/or meta positions in the arylacetic moiety and the pyrrolidino or dimethylamino basic groups are required to optimize biological activity. The lead compounds 28, 30, and 48 are among the most potent antinociceptive agents (ED50 ca. 0.020 microM/kg sc) and kappa ligands (Ki(kappa) ca. 0.20 nM) identified so far.

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“…The reaction mixture was refluxed for 3 h under stirring and was then cooled to ambient temperature. The precipitated solid was filtered and dried to afford compound 3 [ 44 ] in 90% yield as a white solid (m.p. 266–268 °C), which was pure enough to be used for further reactions.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Spectroscopic Characterization and Antimicrobial Potential of Certain New Isatin-Indole Molecular Hybrids

2017

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Molecular hybridization has a wide application in medicinal chemistry to obtain new biologically active compounds. New isatin-indole molecular hybrids 5a–n have been synthesized and characterized by various spectroscopic tools. The in vitro antimicrobial potential of the prepared compounds 5a–n was assessed using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against a panel of Gram-negative bacteria, Gram-positive bacteria and fungi. Most of the synthesized compounds 5a–n showed weak activities against Gram-negative bacteria while compounds 5b and 5c exhibited good activities against Gram-positive bacteria. On the other hand, compound 5j emerged as the most active compound towards Candida albicans (C. albicans), with an MIC value of 3.9 µg/mL, and compound 5g as the most active congener towards Asperagillus niger (A. niger), with an MIC value of 15.6 µg/mL. Moreover, compound 5h manifested the best anti-P. notatum effect, with an MIC value of 7.8 µg/mL, making it equipotent with compound 5g.

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Synthesis of indole-2-carbaldehydes, 2-(2-aminoethyl)- and 2-(2-aminopropyl)-indoles

Cited by 6 publications

References 0 publications

Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity

Synthesis and Biological Evaluation of Indolyl-Pyridinyl-Propenones Having Either Methuosis or Microtubule Disruption Activity

(1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: members of a novel class of very potent .kappa. opioid analgesics

Synthesis, Spectroscopic Characterization and Antimicrobial Potential of Certain New Isatin-Indole Molecular Hybrids

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