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 language | English |
|---|---|
| Pages (from-to) | 4337-4344 |
| Number of pages | 8 |
| Journal | Medicinal Chemistry Research |
| Volume | 23 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - Oct 1 2014 |
| Externally published | Yes |
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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 journal › Article
}
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
AN - SCOPUS:85027949255
VL - 23
SP - 4337
EP - 4344
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
SN - 1054-2523
IS - 10
ER -