A versatile synthetic route to 11H-indolo[3,2-c]isoquinolines

Qu, Ji; Kumar, Naresh; Alamgir, Mahiuddin; Black, David StC.

doi:10.1016/j.tetlet.2009.07.107

Cited by 21 publications

(12 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The crude product was purified by column chromatography on silica gel using hexane–EtOAc (2:1) as the eluent to give ( E )-1-(1 H -indol-3-yl)ethanone oxime as a white solid (797 mg, 92%). 20 The oxime was dissolved in ethanol (6 mL) followed by addition of conc. H 2 SO 4 (several drops).…”

Section: Methodsmentioning

confidence: 99%

“…The combined organic layers were washed with brine (20 mL), dried over Na 2 SO 4 , and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using CHCl 3 /MeOH (10:1) as the eluent to give 1-(3-amino-1 H -indol-1-yl)ethanone ( 20b ) 20 as a dark-green solid (310 mg, 51%). Then the final compound 21b was obtained as a dark-green solid (380 mg, 25% over three steps) following the general procedure.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

et al. 2012

View full text Add to dashboard Cite

In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against T. gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2-hydroxybenzamide 1a against T. gondii as described elsewhere.1 Synthesis of a compound set was guided by T. gondii SAR with 1r found to be superior for T. gondii, also active against Thai and Sierra Leone strains of P. falciparum, and with superior ADMET properties as described elsewhere.1 Herein, synthesis methods and details of the chemical analysis of the compounds in this series are described. Further, this series of N-benzoyl-2-hydroxybenzamides was re-purposed for testing against four other protozoan parasites: T. b. rhodesiense, T. cruzi, L. donovani, and P. falciparum (K1 isolate). Structure-activity analyses led to the identification of compounds in this set with excellent anti-leishmanial activity (compound 1d). Overall, compound 1r was the best and had activity 21-fold superior to that of the standard anti-malarial drug chloroquine against the K1 P. falciparum isolate.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

et al. 2012

View full text Add to dashboard Cite

show abstract

“…The accurate calculated m/z values for these compounds, nevertheless, represent in each case a closet fit consistent with the assigned molecular structures. Whereas the 2-arylindole-3-acetoximes undergo acid-mediated Beckmann rearrangement into 3-acetamido-2-arylindoles with ease [21], the analogous oximes derived from the trifluoroacetyl derivatives are generally stable towards rearrangement into amides [22]. With this literature precedent in mind, we subjected compounds 2a-d to trifluoroacetic acid-mediated Beckmann rearrangement under reflux for 2 h following the literature precedent [11].…”

Section: Synthesismentioning

confidence: 99%

A Study of the Crystal Structure and Hydrogen Bonding of 3-Trifluoroacetyloxime Substituted 7-Acetamido-2-aryl-5-bromoindoles

Mphahlele

2018

Crystals

View full text Add to dashboard Cite

Abstract:The 7-acetyl-2-aryl-5-bromo-3-(trifluoroacetyl)indoles 1a-d were reacted with hydroxylamine hydrochloride (2.2 equiv.) in the presence of pyridine in ethanol under reflux to afford the corresponding diketo oxime derivatives 2a-d.Beckmann rearrangement of the latter with trifluoroacetic acid under reflux afforded the corresponding 7-acetamido-2-aryl-5-bromo-3-(trifluoroacetyloxime)indoles 3a-d. The structures of the prepared compounds were characterized using a combination of NMR ( 1 H & 13 C), IR, and mass spectrometric techniques. The molecular structure of the 3-trifluoroacetyloxime substituted 7-acetamido-2-aryl-5-bromoindoles was unambiguously confirmed by the single crystal X-ray diffraction data of 3d. Structural studies of 3d in the solid state by X-ray crystallography provided evidence of hydrogen bonding networks and π-stacking of the indole moiety. Compound 3d was crystallized in the trigonal space group R-3:H with unit cell dimensions a = 25.1614(13), b = 25.1614(13), c = 17.3032(9) Å, α = β = 90 • , γ = 120 • , V = 9486.9(11) Å 3 , Z = 6. The density functional theory (DFT) structural parameters (bond lengths, bond angles, and torsion angles) of the optimized geometry calculated using the B3LYP/6-311G basis set were found to compare favourably with those of the X-ray crystal structure.

show abstract

“…19 The title compounds 5a-h were synthesized by microwave-assisted four-component synthesis with good yields (73-84 %) ( Table I). 19 The title compounds 5a-h were synthesized by microwave-assisted four-component synthesis with good yields (73-84 %) ( Table I).…”

Section: Chemistrymentioning

confidence: 99%

Microwave-assisted multi-component synthesis of 3’-indolyl substituted pyrano[2,3-c]pyrazoles and their antimicrobial activity

Kathrotiya

Patel

2012

JSCS

View full text Add to dashboard Cite

A series of pyrano[2,3-c]pyrazole derivatives of indole was synthesized by multi-component reactions using the conventional and microwave irradiation approach. Particularly valuable features of this method include high yield, broad substrate scope, shorter reaction times and straightforward procedure. Antimicrobial screening of the synthesized derivatives against eight human pathogens, namely Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli, Aspergillus fumigatus and Candida albicans, was realized by employing the broth microdilution minimum inhibition concentration method, as recommended by National Committee for Clinical Laboratory Standards (NCCLS).Серија деривата пирано[2,3-c]пиразола синтетисана је конвенционалним поступцима и под дејством микроталаса. Поступак са микроталасима карактеришу висок принос, широк опсег супстрата који могу да се користе, краће реакционо време и директан поступак. Извршено је тестирање антимикробне активности синтетисаних једињења према осам патогена Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli, Aspergillus fumigatus и Candida albicans поступком микроразблаживања у бујону према препоруци NCCLS. (Примљено 5. августа, ревидирано 19. октобра 2011)

show abstract

A versatile synthetic route to 11H-indolo[3,2-c]isoquinolines

Cited by 21 publications

References 25 publications

Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

Synthesis, Biological Evaluation, and Structure–Activity Relationships of N-Benzoyl-2-hydroxybenzamides as Agents Active against P. falciparum (K1 strain), Trypanosomes, and Leishmania

A Study of the Crystal Structure and Hydrogen Bonding of 3-Trifluoroacetyloxime Substituted 7-Acetamido-2-aryl-5-bromoindoles

Microwave-assisted multi-component synthesis of 3’-indolyl substituted pyrano[2,3-c]pyrazoles and their antimicrobial activity

Contact Info

Product

Resources

About