Abstract
A series of novel coumarin derivatives were synthesized from 6-hydroxy-7-methoxy-4-methyl coumarin which was isolated from the aerial parts of the Egyptian medicinal plant Ammi majus L. (Apiaceae). The key intermediate 3-amino-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile (3c) was obtained in one-pot synthesis by treating α-cyanocinnamonitrile (1-c) with the natural compound: 6-hydroxy-7-methoxy-4-methyl coumarin (2). Chemical, elemental and spectroscopic evidences confirmed the structures of the synthesized compounds. Some of the newly synthesized compounds exhibited better anti-inflammatory activities at low concentrations compared with indomethacin as positive control.
Similar content being viewed by others
References
Bedair AH, Nagwa AE, Abd El-Latif MS, Fakery AH, El-Agrody AM (2000) 4-Hydroxy coumarin in heterocy-clic synthesis. Part III: Synthesis of some new pyrano [2,3-d] [1,2,4] traizolo [1,5-c] pyrimidines and pyrimido [1,6-b] [1,2,4]–triazine derivatives. lLFarmaco 55:708–714
Bianchi G, Tava A (1987) Synthesis of (2R) (+)-2, 3-dihydro-2, 6-dimethyl-4H-pyran-one, a homologue of pheromones of a species in the hepialid family. Agric Biol Chem 51:2001–2002
Brown D, Katritzky AR, Rees CW (1984) Comprehensive heterocyclic chemistry 3. Pergamon Press, Oxford, p 443
Buhl SN, Jackson KY (1978) Optimal conditions and comparison of lactate dehydrogenase catalysis of the lactate to pyruvate to lactate reactions in human serum at 25, 30 and 37°C. Clin Chem 24:828–835
Dell CP, Smith CW (1993) Ant proliferative derivatives of 4H-naphtho [1, 2- b] pyran and process for their preparation. Eur Pat. 537:94, 9, 21; ref Chem Abstr (1993), 119, 139102d
Domenjoz R, Schwarz (1952) Med Wochschr 82:1023
Eiden F, Denk F (1991) Synthesis and CNS activity of pyrane derivatives: 6, 8-dioxa bicyclo (3, 2, 1)-octanes. Arch Pharm Weinheim Ger 324:353–354
El-Agrody AM, El-Hakim MH, Abd El-Latif MS, Fakery AH, El-Sayed EM, El-Ghareab KA (2000) Synthesis of pyrano[2,3-d]pyrimidine and pyrano[3,2-e] [1,2,4]traizolo[2,3-c]pyrimidine derivatives with promising antibacterial activities. Acta Pharm 50:111–120
El-Agrody AM, Abd El-Latif MS, El-Hady NA, Fakery AH, Bedair AH (2001) Heteroaromatization with hydroxy coumarin. Part II: Synthesis of some new pyrano[2,3-d][1,2,4]traizolo [1,5-c] pyrimidines and pyrimido [1,6-b][1,2,4]-tri-azine derivatives. Molecules 6:519–527
El-Gaby MSA, Abdel-Gawad SM, Ghorab MM, Heiba HI, Aly HM (2006) Synthesis and biological activity of some novel thieno[2,3-b]quinoline, quinolino[3′,2′:4,5] thieno[3,2-d]pyrimidine and pyrido[2′,3′:4,5] thieno[2,3-b]quinoline derivatives. Phosphorus Sulfur Silicon 181:279–297
Fiala S, Fiala AE, Dixon B (1972) Gamma glutamyl transpeptidase in transplantable chemically induced rat hepatomas and spontaneous mouse hepatomas. J Natl Cancer Inst 48:1393
Finney DJ (1964) Statistical methods in biological assay. Charles Griffen & Company Limit, London
Hiramoto K, Nasuhara A, Michiloshi K, Kato T, Kikugawa K (1997) DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one(DDMP). A Maillard reaction product of glucose and glycine. Mutat Res 395:47–56
Hren J, Po_zgan F, Buni CA, Parvulescu VI, Polanc S, Ko_cevar M (2009) An expeditious synthesis of b-pyrimidyl-a, b-didehydro-a-amino acid derivatives and pyrano[2,3-d]pyrimidines using microwave-assisted conditions. Tetrahedron 65:8216–8221
Hussein HEMA, Jamil K, Rao M (2001) Preliminary studies on the hypoglycemia effect of abromaaugustain alloxan diabetic rats. Ind J clin Biochem 16(1):77–80
Ismail ZH, Ghorab MM, Mohamed EMA, Aly HM, El-Gaby MSA (2008) Antitumor activity of some novel 1, 2, 5-thiadiazole derivatives. Phosphorus Sulfur Silicon 183:2541–2554
King EJ, Armstrong AR (1988) Calcium, phosphorus and phosphate. In: Varley H (ed) In practical clinical biochemistry. CBS Publishers, New Delhi, p 458
Lavergne N, Volkman M, Maki JE, Yoder R, Trepanier LA (2005) Evaluation of the clinical, immunologic, and biochemical effects of sulfamethoxazole-nitroso administration to dogs: a pilot study. Toxicology 208:63–72
Marklund S, Marklund D (1974) Involvement of the superoxide anion radical in the autoxidation of pyrogallol and a convenient assay for superoxide dismutase. Eur J Biochem 47:469–476
Martinez-Grau A, Marco LJ (1997) Friedlander reaction on 2-amino-3-cyano-4H-pyrans, synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analogues. Bioorg Med Chem Lett 7:3165–3170
Paglia D, Valentine W (1967) Studies on the quantitative and qualitative characterization of erythrocyte glutathione peroxidase. J Lab Clin Med 70:158–164
Prikazchikova LP, Khutova BM, Vladimirtsev IF, Boldyrev IV, Zhuravskaya NI (1975) Fiziol. Akt. Veshchestva. 7, 84. ref. Chem. Abstr. 83,127346 m
Reitman S, Frankel A (1975) A colorimetric method for the determination of serum glutamic oxaloacetic acid and glutamic pyruvic transaminases. Am J Clin Pathol 28:56–62
Selim YA, Ouf NH (2012) Anti-inflammatory new coumarin from the Ammi majus. L. Org Med Chem Lett 2(1):1–4
Shishoo CJ, Devani MB, Ullas GV, Ananthan S, Bhadti VS (1981) Studies in the synthesis and interconversion of isomeric triazolopyrimidines. J Heterocycl Chem 18:43–46
Taylor R, Cleasby NA, Singh O, Skarzynski T, Wonacott AJ, Smith PW, Sollis SL, Howes PD, Cherry PC, Bethell R, Colman P, Varghese J (1998) Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidases from influenza virus types A and B. J Med Chem 41:798–807
Uchiyama M, Mihara M (1978) Determination of malonaldehyde precursor in tissues by thiobarbituric acid. Anal Biochem 86:271
Van Kampen EJ, Zijlstra WJ (1961) Standardization of hemoglobinometry II. The hemoglobin cyanide method. Clin Chim Acta 6:538–543
Yang JL, Jan MH, Chang CW, Lin JJ (2012) Effectiveness of the end-range mobilization and scapular mobilization approach in a subgroup of subjects with frozen shoulder syndrome: a randomized control trial. Man Ther 17(1):47–52
Yu J, Wang H, Hanqing (2005) Green synthesis of pyrano [2, 3-d]-pyrimidine derivatives in ionic liquids. Synth Commun 35:3133–3140
Acknowledgments
The authors gratefully acknowledge the financial support by Greece and are thankful to the Lab. of organic chemistry (natural product synthesis), Department of Chemistry, Faculty of science Aristotle University of Thessaloniki, Thessaloniki, Greece for the assistance in the performance of some experiments of 1D&2D NMR & MS spectral analyses.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ouf, N.H., Selim, Y.A., Sakran, M.I. et al. Synthesis of pyranochromene and pyranopyrimidine derivatives from substituted natural coumarin isolated from Ammi majus L. and their biological evaluation. Med Chem Res 23, 1180–1188 (2014). https://doi.org/10.1007/s00044-013-0724-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-013-0724-z