Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Ghosh, Arun K.

doi:10.1021/jo101606g

Cited by 32 publications

(27 citation statements)

References 163 publications

(344 reference statements)

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“…This arbitrary solubility trend in benzenemethanesulfonamide is a strong indication that insertion of a sp 3 hybridized carbon between the phenyl and SO 2 unit …”

Section: Resultsmentioning

confidence: 99%

“…Over the years, sulfonamides have been in clinical use [1,2] and are known to represent a class of medicinally important compounds [3][4][5] which are extensively used as antibacterial agents [6][7][8]. Sulfonamide has played a historically fundamental role in the advancement of structure-activity relationships [9] and potential utility of pharmacokinetics in drug design [10].…”

Section: Introductionmentioning

confidence: 99%

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Ecofriendly Synthesis in Aqueous Medium: An Expeditious Approach to New N,N-Diethyl Amide Bearing Benzenemethanesulfonamides

Ajani¹,

Familoni²,

Echeme³

et al. 2013

TOOCJ

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An highly expeditious synthetic approach for the synthesis of benzenemethanesulfonamides (1a-k) and their new corresponding N,N-diethyl substituted amido moieties (2a-k) has been achieved in aqueous medium at room temperature. The reaction condition was thoroughly optimized thereby allowing significant rate enhancement and resulting into excellent yields. The chemical structures of the successful candidates were confirmed using elemental analytical and spectroscopic data such as IR, 1 H NMR, 13 C NMR and some selected mass spectral data. Graphical AbstractEnvironmental friendly synthesis of new N,N-diethyl-substituted-2-(phenylmethylsulfo namido)alkanamide derivatives was achieved in aqueous medium via synthetic modification of the benzenemethanesulfonamide precursors.

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“…This arbitrary solubility trend in benzenemethanesulfonamide is a strong indication that insertion of a sp 3 hybridized carbon between the phenyl and SO 2 unit …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ecofriendly Synthesis in Aqueous Medium: An Expeditious Approach to New N,N-Diethyl Amide Bearing Benzenemethanesulfonamides

Ajani¹,

Familoni²,

Echeme³

et al. 2013

TOOCJ

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“…This structurally simple C 2 symmetry case was compared with NMR spectroscopic parameters to probe the behavior as chelate complex with Cu(I). The configuration of 1 analogs was extensively investigated in many references [47][48][49][50][51][52][53]. The present VCD study is original on such chiral molecules.…”

Section: Introductionmentioning

confidence: 98%

Conformational Analysis in Solution of a Chiral BisoxazolineMolecule: Vibrational Circular Dichroism Spectroscopy and DensityFunctional Theory Study

Aamouche

Stephens

2011

International Journal of Spectroscopy

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The conformations of the chiral bisoxazoline: 2,2 -methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (also named IndaBOX), have been studied. Density functional theory (DFT) calculations identify four inequivalent stable conformations. Two, I and II have, C 2 symmetry; two, III and IV, have C 1 symmetry. The electronic energies of I-IV are ordered: I < II < III < IV. The span in energy is <1.0 kcal/mole. Vibrational unpolarised absorption and circular dichroism spectra have been predicted for the four conformations using DFT. Comparison of population-weighted spectra to experimental spectra of CHCl 3 and CDCl 3 solutions in mid-IR region strongly supports the DFT predictions of the number, structures, and relative energies of the conformations of IndaBOX. This shows that DFT predicts spectra with a high degree of reliability. We will undoubtedly illustrate the advantage added by vibrational circular dichroism spectroscopy in conformational analysis and in the absolute configuration determination.

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“…This design concept is inspired by the occurrence of numerous bioactive natural products with polyether subunits. 16,17 Our laboratory reported a range of exceptionally potent PIs with intriguing molecular features such as TMC-114, TMC126, GRL-06579, GRL-02031, and GRL-519. 18,19,20 These inhibitors show broad-spectrum antiviral activity against multidrug-resistant HIV-1 variants and show high genetic barrier to resistance.…”

Section: Introductionmentioning

confidence: 99%

Design of novel HIV-1 protease inhibitors incorporating isophthalamide-derived P2-P3 ligands: Synthesis, biological evaluation and X-ray structural studies of inhibitor-HIV-1 protease complex

Ghosh

Brindisi

Nyalapatla

et al. 2017

Bioorganic & Medicinal Chemistry

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Based upon molecular insights from the X-ray structures of inhibitor-bound HIV-1 protease complexes, we have designed a series of isophthalamide-derived inhibitors incorporating substituted pyrrolidines, piperidines and thiazolidines as P2-P3 ligands for specific interactions in the S2–S3 extended site. Compound 4b has shown an enzyme Ki of 0.025 nM and antiviral IC50 of 69 nM. An X-ray crystal structure of inhibitor 4b-HIV-1 protease complex was determined at 1.33 Å resolution. We have also determined X-ray structure of 3b-bound HIV-1 protease at 1.27 Å resolution. These structures revealed important molecular insight into the inhibitor–HIV-1 protease interactions in the active site.

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Capturing the Essence of Organic Synthesis: From Bioactive Natural Products to Designed Molecules in Today’s Medicine

Cited by 32 publications

References 163 publications

Ecofriendly Synthesis in Aqueous Medium: An Expeditious Approach to New N,N-Diethyl Amide Bearing Benzenemethanesulfonamides

Ecofriendly Synthesis in Aqueous Medium: An Expeditious Approach to New N,N-Diethyl Amide Bearing Benzenemethanesulfonamides

Conformational Analysis in Solution of a Chiral BisoxazolineMolecule: Vibrational Circular Dichroism Spectroscopy and DensityFunctional Theory Study

Design of novel HIV-1 protease inhibitors incorporating isophthalamide-derived P2-P3 ligands: Synthesis, biological evaluation and X-ray structural studies of inhibitor-HIV-1 protease complex

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