Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline - Isatin hybrids

Manmohan Sharma, Sahil Sharma, Abhishek Buddhiraja, A. K. Saxena, Kunal Nepali, P. M.S. Bedi

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Mia-paca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetylpyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 μM against HeLa Cell line.

Original languageEnglish
Pages (from-to)4337-4344
Number of pages8
JournalMedicinal Chemistry Research
Volume23
Issue number10
DOIs
Publication statusPublished - Oct 1 2014
Externally publishedYes

Fingerprint

Isatin
Cytotoxicity
Cells
Cell Line
Triazoles
HeLa Cells
Click Chemistry
Kidney Neoplasms
Structure-Activity Relationship
Pancreatic Neoplasms
Scaffolds
Uterine Cervical Neoplasms
Inhibitory Concentration 50
Assays
Prostatic Neoplasms

Keywords

  • Cell lines
  • Cytotoxic
  • Hybrids
  • Isatin
  • Molecular hybridization

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline - Isatin hybrids. / Sharma, Manmohan; Sharma, Sahil; Buddhiraja, Abhishek; Saxena, A. K.; Nepali, Kunal; Bedi, P. M.S.

In: Medicinal Chemistry Research, Vol. 23, No. 10, 01.10.2014, p. 4337-4344.

Research output: Contribution to journalArticle

Sharma, Manmohan ; Sharma, Sahil ; Buddhiraja, Abhishek ; Saxena, A. K. ; Nepali, Kunal ; Bedi, P. M.S. / Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline - Isatin hybrids. In: Medicinal Chemistry Research. 2014 ; Vol. 23, No. 10. pp. 4337-4344.
@article{3117a41149044c26961e890a486aab9d,
title = "Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline - Isatin hybrids",
abstract = "Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Mia-paca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetylpyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 μM against HeLa Cell line.",
keywords = "Cell lines, Cytotoxic, Hybrids, Isatin, Molecular hybridization",
author = "Manmohan Sharma and Sahil Sharma and Abhishek Buddhiraja and Saxena, {A. K.} and Kunal Nepali and Bedi, {P. M.S.}",
year = "2014",
month = "10",
day = "1",
doi = "10.1007/s00044-014-1001-5",
language = "English",
volume = "23",
pages = "4337--4344",
journal = "Medicinal Chemistry Research",
issn = "1054-2523",
publisher = "Birkhause Boston",
number = "10",

}

TY - JOUR

T1 - Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline - Isatin hybrids

AU - Sharma, Manmohan

AU - Sharma, Sahil

AU - Buddhiraja, Abhishek

AU - Saxena, A. K.

AU - Nepali, Kunal

AU - Bedi, P. M.S.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Mia-paca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetylpyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 μM against HeLa Cell line.

AB - Numerous reports highlighting the cytotoxic effects of 3,5-diaryl N-acetyl-pyrazolines and isatin tempted us to synthesise conjugates of the functionalities via alkyl armed triazole tetheration. The hybrids were synthesized by click chemistry approach and were evaluated against a panel of cell lines i.e. viz HeLa (cervix cancer), CAKI-I (Renal cancer), PC-3 (Prostate cancer) and Mia-paca-2 (pancreatic cancer). The hybrids were classified into right-handed and left-handed conjugates on the basis of the placement of the isatin ring. The length of the alkyl armed triazole linker was varied from 2 to 6. Structure activity relationship has also been presented. A preliminary cytotoxic assay was performed on the series of 3,5-diaryl N-acetyl-pyrazolines and only the potent 3,5-diaryl N-acetylpyrazolines were selected for their inclusion in the hybrid scaffold. Among the cell lines employed, HeLa cell line was the most sensitive towards the exposure of test compounds. Out of all the compounds evaluated, two right-handed conjugates MI-7b and MI-8b and two left-handed conjugates MI-4b, MI-6b displayed significant cytotoxic potential and exhibited an IC50 range from 1.3 to 3.5 μM against HeLa Cell line.

KW - Cell lines

KW - Cytotoxic

KW - Hybrids

KW - Isatin

KW - Molecular hybridization

UR - http://www.scopus.com/inward/record.url?scp=85027949255&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85027949255&partnerID=8YFLogxK

U2 - 10.1007/s00044-014-1001-5

DO - 10.1007/s00044-014-1001-5

M3 - Article

VL - 23

SP - 4337

EP - 4344

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

SN - 1054-2523

IS - 10

ER -