Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

Muhammad Taha; Nor Hadiani Ismail; Kulsoom Javaid; Syahrul Imran; El Hassane Anouar; Abdul Wadood; Atia-Tul-Wahab; Muhammad Ali; Khalid Mohammed Khan; Syed Muhammad Saad; Fazal Rahim; M. Iqbal Choudhary

doi:10.1016/j.bioorg.2015.09.001

Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

Muhammad Taha
, Nor Hadiani Ismail
, Kulsoom Javaid
, Syahrul Imran
, El Hassane Anouar
, Abdul Wadood
, Atia-Tul-Wahab
, Muhammad Ali
, Khalid Mohammed Khan
, Syed Muhammad Saad
, Fazal Rahim
, M. Iqbal Choudhary

Chemistry

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC₅₀ values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC₅₀ = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of ν_C=O, ν_N=C and ν_CH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds.

Original language	English
Pages (from-to)	24-35
Number of pages	12
Journal	Bioorganic Chemistry
Volume	63
DOIs	https://doi.org/10.1016/j.bioorg.2015.09.001
State	Published - 1 Dec 2015

Keywords

2-Indolcarbohydrazones
Density Functional Theory (DFT)
In silico studies
Structure-activity relationship
α-Glucosidase inhibition

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10.1016/j.bioorg.2015.09.001

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Taha, M., Ismail, N. H., Javaid, K., Imran, S., Anouar, E. H., Wadood, A., Atia-Tul-Wahab, Ali, M., Khan, K. M., Saad, S. M., Rahim, F., & Choudhary, M. I. (2015). Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions. Bioorganic Chemistry, 63, 24-35. https://doi.org/10.1016/j.bioorg.2015.09.001

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title = "Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions",

abstract = "2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds.",

keywords = "2-Indolcarbohydrazones, Density Functional Theory (DFT), In silico studies, Structure-activity relationship, α-Glucosidase inhibition",

author = "Muhammad Taha and Ismail, \{Nor Hadiani\} and Kulsoom Javaid and Syahrul Imran and Anouar, \{El Hassane\} and Abdul Wadood and Atia-Tul-Wahab and Muhammad Ali and Khan, \{Khalid Mohammed\} and Saad, \{Syed Muhammad\} and Fazal Rahim and Choudhary, \{M. Iqbal\}",

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doi = "10.1016/j.bioorg.2015.09.001",

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AU - Taha, Muhammad

AU - Ismail, Nor Hadiani

AU - Javaid, Kulsoom

AU - Imran, Syahrul

AU - Anouar, El Hassane

AU - Wadood, Abdul

AU - Atia-Tul-Wahab,

AU - Ali, Muhammad

AU - Khan, Khalid Mohammed

AU - Saad, Syed Muhammad

AU - Rahim, Fazal

AU - Choudhary, M. Iqbal

PY - 2015/12/1

Y1 - 2015/12/1

N2 - 2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds.

AB - 2-Indolcarbohydrazones 1-28 were synthesized and evaluated for their α-glucosidase inhibitory potential. A varying degree of inhibitory potential with IC50 values in the range of 2.3 ± 0.11-226.4 ± 6.8 μM was observed while comparing these outcomes with the standard acarbose (IC50 = 906.0±6.3μM). The stereochemistry of ten (10) randomly selected compounds (1, 3, 6, 8, 12, 18, 19, 23, 25 and 28) was predicted by Density Functional Theory (DFT). The stability of E isomer was deduced by comparing the calculated and experimental vibration modes of νC=O, νN=C and νCH (CH in -N=CH-R). It was observed that except compound 18, all other compounds were deduced to have E configuration while molecular modeling studies revealed the key interactions between enzyme and synthesized compounds.

KW - 2-Indolcarbohydrazones

KW - Density Functional Theory (DFT)

KW - In silico studies

KW - Structure-activity relationship

KW - α-Glucosidase inhibition

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DO - 10.1016/j.bioorg.2015.09.001

M3 - Article

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EP - 35

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

ER -

Evaluation of 2-indolcarbohydrazones as potent α-glucosidase inhibitors, in silico studies and DFT based stereochemical predictions

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Keywords

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