Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs

European Journal of Medicinal Chemistry

Volumn 77, Issue , 2014, Pages 400-408

  Sánchez Recillas, Amanda ^a   Navarrete Vázquez, Gabriel ^a   Hidalgo Figueroa, Sergio ^a   Rios, María Yolanda ^b   Ibarra Barajas, Maximiliano ^c   Estrada Soto, Samuel ^a  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MORELOS   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Asthma; Coumarins; Natural products; Pharmacophoric group; SAR; Tracheal rings

Indexed keywords

2 OXO 2H CHROMEN 7 YL ACETATE; 2 OXO 2H CHROMEN 7 YL BENZOATE; 2 OXO 2H CHROMENE 6,7 DIYL DIACETATE; 2 OXO 2H CHROMENE 6,7 DIYL DIBENZOATE; 4 METHYL 2 OXO 2H CHROMEN 7 YL ACETATE; 4 METHYL 2 OXO 2H CHROMEN 7 YL BENZOATE; 4 METHYL 7 PROPOXY 2H CHROMEN 2 ONE; 6,7 DIETHOXY 2H CHROMEN 2 ONE; 6,7 DIMETHOXY 2H CHROMEN 2 ONE; 6,7 DIPROPROXY 2H CHROMEN 2 ONE; 7 ETHOXY 2H CHROMEN 2 ONE; 7 ETHOXY 4 METHYL 2H CHROMEN 2 ONE; 7 METHOXY 2H CHROMEN 2 ONE; 7 METHOXY 4 METHYL 2H CHROMEN 2 ONE; 7 PROPROXY 2H CHROMEN 2 ONE; ANTIASTHMATIC AGENT; CARBACHOL; ESCULETIN; ETHYL 2 (2 OXO 2H CHROMEN 7 YLOXY)ACETATE; ETHYL 2 (4 METHYL 2 OXO 2H CHROMEN 7 YLOXY)ACETATE; ETHYL [[6 (2 ETHOXY 2 OXOETHOXY) 2 OXO 2H CHROMEN 7 YL]OXY]ACETATE; HYMECROMONE; THEOPHYLLINE; UMBELLIFERONE; UNCLASSIFIED DRUG; COUMARIN; COUMARIN DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; ASTHMA; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EX VIVO STUDY; MALE; MOLECULAR WEIGHT; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; IN VITRO STUDY; SYNTHESIS; TRACHEA; WISTAR RAT;

ANIMALS; ANTI-ASTHMATIC AGENTS; COUMARINS; DOSE-RESPONSE RELATIONSHIP, DRUG; IN VITRO TECHNIQUES; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; TRACHEA;

EID: 84893638119     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.029     Document Type: Article

References (38)

1. http://ginasthma.org/.
2. http://www.who.int/en/.
3. Y.W. Chin, M.J. Balunas, H.B. Chai, and A.D. Kinghorn Drug discovery from natural sources AAPS Journal 8 2006 E239 E253
4. K.N. Venugopala, and V.B. Odhav Review on natural coumarin lead compounds for their pharmacological activity BioMed Research International 2013 963248 10.1155/2013/963248
5. M.J. Matos, F. Pérez-Cruz, S. Vazquez-Rodriguez, E. Uriarte, L. Santana, F. Borges, and C. Olea-Azar Remarkable antioxidant properties of a series of hydoxy-3-arylcoumarins Bioorganic & Medicinal Chemistry 21 2013 3900 3906
6. R.A. Davis, D. Vullo, A. Maresca, C.T. Supuran, and S.A. Poulsen Natural product coumarins that inhibit human carbonic anhydrases Bioorganic & Medicinal Chemistry 21 2013 1539 1543
7. A.S. Awaad, N.A. Al-Jaber, G.A. Soliman, M.R. Al-Outhman, M.E. Zain, J.E. Moses, and R.M. El-Meligy New biological activities of Casimiroa edulis leaf extract and isolated compounds Phytotherapy Research 26 2012 452 457
8. O.S. Kwon, J.S. Choi, M.N. Islam, Y.S. Kim, and H.P. Kim Inhibition of 5-lipoxygenase and skin inflammation by the aerial parts of Artemisia capillaris and its constituents Archives of Pharmacal Research 34 2011 1561 1569
9. P.J. Dasiewicz, J.M. Conlon, and W.G. Anderson Cardiovascular and vasoconstrictive actions of skate bradykinin in the little skate, Leucoraja erinacea (Elasmobranchii) General and Comparative Endocrinology 174 2011 89 96
10. M. Atmaca, H.M. Bilgin, B.D. Obay, H. Diken, M. Kelle, and E. Kale The hepatoprotective effect of coumarin and coumarin derivates on carbon tetrachloride-induced hepatic injury by antioxidative activities in rats Journal of Physiology and Biochemistry 67 2011 569 576
11. A. Karmase, R. Birari, and K.K. Bhutani Evaluation of anti-obesity effect of Aegle marmelos leaves Phytomedicine 20 2013 805 812
12. S.R. Subramaniam, and E.M. Ellis Neuroprotective effects of umbelliferone and esculetin in a mouse model of Parkinson's disease Journal of Neuroscience Research 91 2013 453 461
13. B. Ramesh, and K.V. Pugalendi Antihyperlipidemic and antidiabetic effects of umbelliferone in streptozotocin diabetic rats Yale Journal of Biology and Medicine 78 2005 189 196
14. J.F. Vasconcelos, M.M. Teixeira, J.M. Barbosa-Filho, M.F. Agra, X.P. Nunes, A.M. Giulietti, R. Ribeiro-Dos-Santos, and M.B. Soares Effects of umbelliferone in a murine model of allergic airway inflammation European Journal of Pharmacology 609 2009 126 131
15. K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, and D.N. Nicolaides Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities Current Pharmaceutical Design 10 2004 3813 3833
16. D. Ramanitrahasimbola, D.A. Rakotondramanana, P. Rasoanaivo, A. Randriantsoa, S. Ratsimamanga, G. Palazzino, C. Galeffi, and M. Nicoletti Bronchodilator activity of Phymatodes scolopendria (Burm.) Ching and its bioactive constituent Journal of Ethnopharmacology 102 2005 400 407
17. M. Iranshahy, and M. Iranshahi Traditional uses, phytochemistry and pharmacology of asafoetida (Ferula assa-foetida oleo-gum-resin)-a review Journal of Ethnopharmacology 134 2011 1 10
18. J.C. Jung, and S. Oh Practical synthesis of hydroxychromenes and evaluation of their biological activity Molecules 17 2012 240 247
19. S. Siddiqui, N.S. Redhu, O.O. Ojo, B. Liu, N. Irechukwu, C. Billington, L. Janssen, and M.L. Moir Emerging airway smooth muscle targets to treat asthma Pulmonary Pharmacology & Therapeutics 26 2013 132 144
20. J.R. Hoult, and M. Payá Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential General Pharmacology 27 1996 713 722
21. C.K. Billington, O.O. Ojo, R.B. Penn, and S. Ito cAMP regulation of airway smooth muscle function Pulmonary Pharmacology & Therapeutics 26 2013 112 120
22. 2+ sparks act as potent regulators of excitation-contraction coupling in airway smooth muscle Journal of Biological Chemistry 285 2010 2203 2210
23. J.H. Jaggar, V.A. Porter, W.J. Lederer, and M.T. Nelson Calcium sparks in smooth muscle American Journal of Physiology - Cell Physiology 278 2000 C235 C256
24. L.B. Bergantin, C.F. Souza, R.M. Ferreira, S.S. Smaili, N.H. Jurkiewicz, A. Caricati-Neto, and A. Jurkiewicz Novel model for "calcium paradox" in sympathetic transmission of smooth muscles: role of cyclic AMP pathway Cell Calcium 54 2013 202 212
25. H. Meurs, T.A. Oenema, L.E. Kistemaker, and R. Gosens A new perspective on muscarinic receptor antagonism in obstructive airways diseases Current Opinion in Pharmacology 13 2013 316 323
26. A.F. Roffel, C.R. Elzinga, and J. Zaagsma Muscarinic M3 receptors mediate contraction of human central and peripheral airway smooth muscle Pulmonary Pharmacology 3 1990 47 51
27. H.C. Huang, C.R. Lee, Y.I. Weng, M.C. Lee, and Y.T. Lee Vasodilator effect of scoparone (6,7-dimethoxycoumarin) from a Chinese herb European Journal of Pharmacology 218 1992 123 128
28. Y.H. Choi, and G.H. Yan Anti-allergic effects of scoparone on mast cell-mediated allergy model Phytomedicine 16 2009 1089 1094
29. H. Hakonarson, and M.M. Grunstein Regulation of second messengers associated with airway smooth muscle contraction and relaxation American Journal of Respiratory and Critical Care Medicine 158 1998 S115 S122
30. I.V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V.A. Palyulin, E.V. Radchenko, N.S. Zefirov, A.S. Makarenko, V.Y. Tanchuk, and V.V. Prokopenko Virtual computational chemistry laboratory-design and description Journal of Computer-Aided Molecular Design 19 2005 453 463
31. http://www.vcclab.org.
32. H. Van de Waterbeemd, D.A. Smith, and B.C. Jones Lipophilicity in PK design: methyl, ethyl, futile Journal of Computer-Aided Molecular Design 15 2001 273 286
33. G. Lunn, B.J. Banks, R. Crook, N. Feeder, A. Pettman, and Y. Sabnis Discovery and synthesis of a new class of opioid ligand having a 3-azabicyclo[3.1.0]hexane core. An example of a 'magic methyl' giving a 35-fold improvement in binding Bioorganic & Medicinal Chemistry Letters 21 2011 4608 4611
34. I.V. Tetko Computing chemistry on the web Drug Discovery Today 10 2005 1497 1500
35. W.L.F. Armarego, and D.D. Perrin Purification of Laboratory Chemicals fourth ed. 1988 Pergamon Oxford (Chapter 1)
36. J.S. Fedan, M.R. Van Scott, and R.A. Johnston Pharmacological techniques for the in vitro study of airways Journal of Pharmacological and Toxicological Methods 45 2001 159 174
37. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Advanced Drug Delivery Reviews 46 2001 3 26
38. http://www.molinspiration.com/cgi-bin/properties/.