Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

Ashraf A. Aly; Alaa A. Hassan; Maysa M. Makhlouf; Mohammed B. Alshammari; Sara Mohamed Naguib Abdel Hafez; Marwa M.M. Refaie; Stefan Bräse; Martin Nieger; Mohamed Ramadan

doi:10.1002/ardp.202000336

Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

Ashraf A. Aly
, Alaa A. Hassan
, Maysa M. Makhlouf
, Mohammed B. Alshammari
, Sara Mohamed Naguib Abdel Hafez
, Marwa M.M. Refaie
, Stefan Bräse
, Martin Nieger
, Mohamed Ramadan

Chemistry

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

1 Scopus citations

Abstract

New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (¹H NMR, ¹³C NMR, two-dimensional NMR, mass spectrometry, elemental analysis, and single-crystal X-ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin-induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin-induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.

Original language	English
Article number	2000336
Journal	Archiv der Pharmazie
Volume	354
Issue number	5
DOIs	https://doi.org/10.1002/ardp.202000336
State	Published - May 2021

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

4-substituted hydrazinecarbothioamides
antihyperglycemic activity
bis(2-(phenylsulfonyl)-ethyl)sulfane
glutathione
malondialdehyde
sulfonylalkylthiosemicarbazide

Access to Document

10.1002/ardp.202000336

Cite this

@article{ad8d6ddb36df4eff87c9f4514fb04fa4,

title = "Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents",

abstract = "New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two-dimensional NMR, mass spectrometry, elemental analysis, and single-crystal X-ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin-induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin-induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.",

keywords = "4-substituted hydrazinecarbothioamides, antihyperglycemic activity, bis(2-(phenylsulfonyl)-ethyl)sulfane, glutathione, malondialdehyde, sulfonylalkylthiosemicarbazide",

author = "Aly, \{Ashraf A.\} and Hassan, \{Alaa A.\} and Makhlouf, \{Maysa M.\} and Alshammari, \{Mohammed B.\} and \{Mohamed Naguib Abdel Hafez\}, Sara and Refaie, \{Marwa M.M.\} and Stefan Br{\"a}se and Martin Nieger and Mohamed Ramadan",

note = "Publisher Copyright: {\textcopyright} 2021 Deutsche Pharmazeutische Gesellschaft",

year = "2021",

month = may,

doi = "10.1002/ardp.202000336",

language = "English",

volume = "354",

journal = "Archiv der Pharmazie",

issn = "0365-6233",

publisher = "Wiley-VCH Verlag",

number = "5",

}

TY - JOUR

T1 - Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

AU - Aly, Ashraf A.

AU - Hassan, Alaa A.

AU - Makhlouf, Maysa M.

AU - Alshammari, Mohammed B.

AU - Mohamed Naguib Abdel Hafez, Sara

AU - Refaie, Marwa M.M.

AU - Bräse, Stefan

AU - Nieger, Martin

AU - Ramadan, Mohamed

PY - 2021/5

Y1 - 2021/5

N2 - New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two-dimensional NMR, mass spectrometry, elemental analysis, and single-crystal X-ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin-induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin-induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.

AB - New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two-dimensional NMR, mass spectrometry, elemental analysis, and single-crystal X-ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin-induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin-induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.

KW - 4-substituted hydrazinecarbothioamides

KW - antihyperglycemic activity

KW - bis(2-(phenylsulfonyl)-ethyl)sulfane

KW - glutathione

KW - malondialdehyde

KW - sulfonylalkylthiosemicarbazide

UR - https://www.scopus.com/pages/publications/85099262360

U2 - 10.1002/ardp.202000336

DO - 10.1002/ardp.202000336

M3 - Article

C2 - 33410162

AN - SCOPUS:85099262360

SN - 0365-6233

VL - 354

JO - Archiv der Pharmazie

JF - Archiv der Pharmazie

IS - 5

M1 - 2000336

ER -

Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents

Abstract

UN SDGs

Keywords

Access to Document

Other files and links

Fingerprint

Cite this