Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Brijesh Kumar Srivastava; Rina Soni; Jayendra Z. Patel; Satadru Jha; Sandeep A. Shedage; Neha Gandhi; Kalapatapu V.V.M. Sairam; Vishwanath Pawar; Nisha Sadhwani; Prasenjit Mitra; Mukul R. Jain; Pankaj R. Patel

doi:10.1016/j.bmcl.2008.06.045

Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Brijesh Kumar Srivastava^*
, Rina Soni
, Jayendra Z. Patel
, Satadru Jha
, Sandeep A. Shedage
, Neha Gandhi
, Kalapatapu V.V.M. Sairam
, Vishwanath Pawar
, Nisha Sadhwani
, Prasenjit Mitra
, Mukul R. Jain
, Pankaj R. Patel

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO₂ group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.

Original language	English
Pages (from-to)	3882-3886
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2008.06.045
Publication status	Published - 15-07-2008

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Kumar Srivastava, B., Soni, R., Patel, J. Z., Jha, S., Shedage, S. A., Gandhi, N., Sairam, K. V. V. M., Pawar, V., Sadhwani, N., Mitra, P., Jain, M. R., & Patel, P. R. (2008). Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist. Bioorganic and Medicinal Chemistry Letters, 18(14), 3882-3886. https://doi.org/10.1016/j.bmcl.2008.06.045

Kumar Srivastava, Brijesh ; Soni, Rina ; Patel, Jayendra Z. et al. / Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist. In: Bioorganic and Medicinal Chemistry Letters. 2008 ; Vol. 18, No. 14. pp. 3882-3886.

@article{774a2b6c7b3a4b43a5703dcbe0e5fac2,

title = "Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist",

abstract = "Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO2 group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.",

author = "\{Kumar Srivastava\}, Brijesh and Rina Soni and Patel, \{Jayendra Z.\} and Satadru Jha and Shedage, \{Sandeep A.\} and Neha Gandhi and Sairam, \{Kalapatapu V.V.M.\} and Vishwanath Pawar and Nisha Sadhwani and Prasenjit Mitra and Jain, \{Mukul R.\} and Patel, \{Pankaj R.\}",

year = "2008",

month = jul,

day = "15",

doi = "10.1016/j.bmcl.2008.06.045",

language = "English",

volume = "18",

pages = "3882--3886",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

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number = "14",

}

Kumar Srivastava, B, Soni, R, Patel, JZ, Jha, S, Shedage, SA, Gandhi, N, Sairam, KVVM, Pawar, V, Sadhwani, N, Mitra, P, Jain, MR & Patel, PR 2008, 'Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist', Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 14, pp. 3882-3886. https://doi.org/10.1016/j.bmcl.2008.06.045

Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist. / Kumar Srivastava, Brijesh; Soni, Rina; Patel, Jayendra Z. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 18, No. 14, 15.07.2008, p. 3882-3886.

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

TY - JOUR

T1 - Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

AU - Kumar Srivastava, Brijesh

AU - Soni, Rina

AU - Patel, Jayendra Z.

AU - Jha, Satadru

AU - Shedage, Sandeep A.

AU - Gandhi, Neha

AU - Sairam, Kalapatapu V.V.M.

AU - Pawar, Vishwanath

AU - Sadhwani, Nisha

AU - Mitra, Prasenjit

AU - Jain, Mukul R.

AU - Patel, Pankaj R.

PY - 2008/7/15

Y1 - 2008/7/15

N2 - Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO2 group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.

AB - Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO2 group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.

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SN - 0960-894X

VL - 18

SP - 3882

EP - 3886

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 14

ER -

Kumar Srivastava B, Soni R, Patel JZ, Jha S, Shedage SA, Gandhi N et al. Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist. Bioorganic and Medicinal Chemistry Letters. 2008 Jul 15;18(14):3882-3886. doi: 10.1016/j.bmcl.2008.06.045

Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Abstract

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