Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

D. Rambabu; Naveen Mulakayala; Ismail; K. Ravi Kumar; G. Pavan Kumar; Chaitanya Mulakayala; Chitta Suresh Kumar; Arunasree M. Kalle; M. V. Basaveswara Rao; Srinivas Oruganti; Manojit Pal

doi:10.1016/j.bmcl.2012.08.082

Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

D. Rambabu, Naveen Mulakayala, Ismail, K. Ravi Kumar, G. Pavan Kumar, Chaitanya Mulakayala, Chitta Suresh Kumar, Arunasree M. Kalle, M. V. Basaveswara Rao, Srinivas Oruganti, Manojit Pal

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

21 Scopus citations

Abstract

A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein.

Original language	English
Pages (from-to)	6745-6749
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	21
DOIs	https://doi.org/10.1016/j.bmcl.2012.08.082
State	Published - 1 Nov 2012
Externally published	Yes

Keywords

Coumarin
Cyclooxygenase
Docking
X-ray

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2012.08.082

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Rambabu, D., Mulakayala, N., Ismail, Ravi Kumar, K., Pavan Kumar, G., Mulakayala, C., Kumar, C. S., Kalle, A. M., Basaveswara Rao, M. V., Oruganti, S., & Pal, M. (2012). Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors. Bioorganic and Medicinal Chemistry Letters, 22(21), 6745-6749. https://doi.org/10.1016/j.bmcl.2012.08.082

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title = "Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors",

abstract = "A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein.",

keywords = "Coumarin, Cyclooxygenase, Docking, X-ray",

author = "D. Rambabu and Naveen Mulakayala and Ismail and \{Ravi Kumar\}, K. and \{Pavan Kumar\}, G. and Chaitanya Mulakayala and Kumar, \{Chitta Suresh\} and Kalle, \{Arunasree M.\} and \{Basaveswara Rao\}, \{M. V.\} and Srinivas Oruganti and Manojit Pal",

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doi = "10.1016/j.bmcl.2012.08.082",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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Rambabu, D, Mulakayala, N, Ismail, Ravi Kumar, K, Pavan Kumar, G, Mulakayala, C, Kumar, CS, Kalle, AM, Basaveswara Rao, MV, Oruganti, S & Pal, M 2012, 'Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors', Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 21, pp. 6745-6749. https://doi.org/10.1016/j.bmcl.2012.08.082

TY - JOUR

T1 - Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

AU - Rambabu, D.

AU - Mulakayala, Naveen

AU - Ismail,

AU - Ravi Kumar, K.

AU - Pavan Kumar, G.

AU - Mulakayala, Chaitanya

AU - Kumar, Chitta Suresh

AU - Kalle, Arunasree M.

AU - Basaveswara Rao, M. V.

AU - Oruganti, Srinivas

AU - Pal, Manojit

PY - 2012/11/1

Y1 - 2012/11/1

N2 - A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein.

AB - A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy)propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein.

KW - Coumarin

KW - Cyclooxygenase

KW - Docking

KW - X-ray

UR - https://www.scopus.com/pages/publications/84867574924

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DO - 10.1016/j.bmcl.2012.08.082

M3 - Article

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AN - SCOPUS:84867574924

SN - 0960-894X

VL - 22

SP - 6745

EP - 6749

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 21

ER -

Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

Abstract

Keywords

ASJC Scopus subject areas

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