Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivatives

Hegab, Mohamed; Yousef, Nabil; Nour, Hany; Ellithey, Mohey; Arbid, Mahmoud

doi:10.2478/v10007-007-0042-4

Abstract

Some new hydrazono 5a,b, thiosemicarbazono 6a-c, and oximo chromenes 7a-c were prepared via the reaction of the corresponding β-chlorocarbaldehyde 3 with hydrazine, aromatic hydrazine, thiosemicarbazide and hydroxylamine hydrochloride, respectively. In addition, ether derivatives 8a-h were prepared from the corresponding aldoximes 7a-c. The new products were tested for anti-inflammatory and ulcerogenic score activities compared to indomethacin.

References

B. C. Sekhar, S. R. Ramadas and D. V. Ramana, β-Halovinylaldehydes as versatile reactive intermediates in the syntheses of condensed fused ring polycyclic heterocycles, Heterocycles53 (2000) 941-977.10.3987/REV-99-527
Search in Google Scholar
T. Aubert, M. Farnier, I. Meunier and R. Guilard, Synthesis of dipyrazolo[3,4-b:4',3'-f]azepines and dithieno[2,3-b:3',2'-f]azepines from 1-substituted 2,7-dichloro-4,5-dihydro-1H-azepine-3,6-dicarbaldehydes, J. Chem. Soc. Perkin Trans. I 1989, 2095-2098; DOI: 10.1039/p1989002095.
Search in Google Scholar
M. I. El-Deen, Use of 3-(2-formyl-1-chlorovinyl)coumarin in the synthesis of pyrazole and pyrimidine derivatives and salicylaldehyde azine, Chin. J. Chem.17 (1999) 391-397.10.1002/cjoc.19990170412
Search in Google Scholar
M. I. El-Deen, K. H. Abd El-Fattah and I. A. El-Gohary, Synthesis and investigation of mass spectra of 3-[5'-(2'-substituent)thienyl]benzo[5,6]coumarines, Phosphorus Sulfur Silicon Relat. Elem.178 (2003) 1463-1476; DOI: 10.1080/10426500307879.10.1080/10426500307879
Search in Google Scholar
K. Clarke, D. N. Gregory and R. M. Scrowston, Naphtho[1,2-b]thiophene. Part 1. Preparation and electrophilic substitution, J. Chem. Soc. Perkin Trans. I1973, 2956-2960; DOI: 10.1039/p19730002956.10.1039/p19730002956
Search in Google Scholar
M. I. Hegab and M. M. Abdulla, 4-Chloro-2,2-disubstituted chromene-3-carboxaldehyde: Synthesis of some fused polycyclic heterocycles as anti-inflammatory, analgesic, anticonvulsant, and antiparkinsonian agents, Arch. Pharm. Chem. Life Sci.339 (2006) 41-47; DOI: 10.1002/ardp.200500124.10.1002/ardp.20050012416411175
Search in Google Scholar
R. A. Pawar and A. P. Rajput, Studies on the Vilsmeier-Haack reaction. A versatile new synthesis of 4-chloro-2-phenylaminothiazole-5-carboxaldehyde and related fused heterocyclic compounds, Indian J. Chem. B28 (1989) 866-867.
Search in Google Scholar
J. V. Dijk and J. M. A. Zwagemakers, Oxime ether derivatives, A new class of nonsteroidal anti-inflammatory compounds, J. Med. Chem.20 (1977) 1199-1206; DOI: 10.1021/jm00219a018.10.1021/jm00219a018926121
Search in Google Scholar
H. Chowdhury and V. S. Saxean, Synthesis and insect growth regulatory activity of alkoxy-substituted benzaldoxime ethers, J. Agr. Food Chem.46 (1998) 731-736; DOI: 10.1021/jf970062h.10.1021/jf970062h10554306
Search in Google Scholar
D. P. Jindal, R. Chattopadhaya, S. Guleria and R. Gupta, Synthesis and antineoplastic activity of 2-alkylaminoethyl derivatives of various steroidal oximes, Eur. J. Med. Chem.38 (2003) 1025-1034; DOI: 10.1016/j.ljmech.2003.09.002.
Search in Google Scholar
C. Kirilmis, M. Koca, A. Cukurovali, M. Ahmedzade and C. Kazaz, Synthesis, reactivity and biological activity of novel bisbenzofuran-2-yl-methanone derivatives, Molecules10 (2005) 1399-1408.10.3390/10111399614751818007535
Search in Google Scholar
F. A. G. El-Essawy, S. M. Yassin, I. A. El-Sakka, A. F. Khattab, I. Støfte, J. Møller and A. Senning, Cycloaddition with 2,2-dialkyl-3-thioxochroman-4-one S-sulfides including an unprecedented [3+5] cycloaddition, J. Org. Chem.63 (1998) 9840-9845; DOI: 10.1021/jo9815347.
Search in Google Scholar
H. J. Kabbe, Eine einfache Synthese von 4-Chromanonen, Synthesis1978, 886-887; DOI: 10.1055/s-1978-24924.10.1055/s-1978-24924
Search in Google Scholar
Alberola, B. Calvo, A. G. Ortega and R. Pedrosa, Reaction of 4-chlorocoumarin with organometallic reagents. Synthesis of trialkylbenzopyrans, 4-alkylcoumarins and o-hydroxyphenylprop-2-ynyl alcohols, J. Chem. Soc. Perkin Trans I1992, 3075-3080; DOI: 10.1039/p19920003075.10.1039/p19920003075
Search in Google Scholar
T. Eszenyi, T. Tímár and P. Sebók, A novel synthesis of 4-halo-2H-chromenes, Tetrahedron Lett.32 (1991) 827-828; DOI: 10.1016/S0040-4039(00)74898-2.10.1016/S0040-4039(00)74898-2
Search in Google Scholar
M. I. Hegab, A. M. Abdel-Fattah, N. M. Yousef, H. F. Nour, A. M. Mostafa and M. Ellithey, Synthesis, X-ray structure, and pharmacological activity of some 6,6-disubstituted chromeno[4,3-b]-and chromeno[3,4-c]-quinolines, Arch. Pharm. Chem. Life Sci.340 (2007) 396-403; DOI: 10.1002/ardp.200700089.10.1002/ardp.200700089
Search in Google Scholar
M. Hernández-Pérez, R. M. Rabanal, M. C. de la Torre and B. Rodriguez, Analgesic, anti-inflammatory, antipyretic and haematological effects of aethiopinone, and o-naphthoquinone diterpenoid from Salvia aethiopis roots and two hemisynthetic derivatives, Planta Med.61 (1995) 505-509; DOI: 10.1055/s-2006-959358.10.1055/s-2006-959358
Search in Google Scholar
H. Ikuta, H. Shirota, S. Kobayashi, Y. Yamagishi, K. Yamada, I. Yamatsu and K. Katayama, Synthesis and anti-inflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones, J. Med. Chem.30 (1987) 1995-1998; DOI: 10.1021/jm00394a011.10.1021/jm00394a011
Search in Google Scholar
F. Sztaricskai, I. E. Takacs, F. Pusztai, G. Szabo and I. Csipo, Antiulcer effect of the N- and O-β-D-glucopyranosides of 5-aminosalicylic acid, Arch. Pharm.332 (1999) 321-326; DOI: 10.1002/(SICI)1521-4184(19999)332:9<;321::AID-ARDP321>3.3.CO;2-1.10.1002/(SICI)1521-4184(19999)332:9<;321::AID-ARDP321>3.0.CO;2-A
Search in Google Scholar
J. Hlaváč, R. Buchtík, J. Slouka, P. Haradil and I. Wiedermannová, Synthesis of oxo analogs of Lamotrigine and related compounds, Arkivoc (2003) 22-28; ref. Chem. Abstr.140 (2004) 199296p.
Search in Google Scholar
M. C. Pirung and S. V. Pansare, Trityl isothiocyanate support for solid-phase synthesis, J. Comb. Chem.3 (2001) 90-96; DOI: 10.1021/cc000072m.10.1021/cc000072m
Search in Google Scholar

Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivatives

Abstract

Paradigm

My account