Novel anti-inflammatory and analgesic agents of 5-chromeno-pyrido[2,3-d]pyrimidine-4-yl derivatives and S-nucleosides analogous

International Journal of Pharmaceutical Sciences Review and Research

Volumn 4, Issue 2, 2010, Pages 25-36

  Babatin, Mohammed M ^a   Said, Madhat M ^b   Hafez, Hend N ^b   El Gazzar, Abdel Rahman B A ^a  

^a AL IMAM MOHAMMAD IBN SAUD ISLAMIC UNIVERSITY IMSIU   (Saudi Arabia)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

5 Chromeno pyrido 2,3 d pyrimidine; Anti inflammatory and Analgesic activities; S Nucleosides

Indexed keywords

5 (4 MORPHOLINOCOUMARIN 3 YL) 2 THIOXO 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 (4 MORPHOLINOCOUMARIN 3 YL) 2 THIOXO 8 DIMETHYL 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 (4 N METHYLPIPRAZINOCOUMARIN 3 YL) 2 THIOXO 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 (4 N METHYLPIPRAZINOCOUMARIN 3 YL) 2 THIOXO 8 DIMETHYL 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 (4 PIPRAZINOCOUMARIN 3 YL) 2 THIOXO 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 (4 PIPRAZINOCOUMARIN 3 YL) 2 THIOXO 8 DIMETHYL 6,7,8,9 TETRAHYDROPYRIMIDO[4,5 B] QUINOLINE 4,6 DIONE; 5 CHROMENO PYRIDO[2,3 D]PYRIMIDIN 4 YL DERIVATIVE; 7 (4 ANISYL) 5 PHENYL 2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 ANISYL) 5 PHENYL 2 (2',3',5' TRI O ACETYL BETA DEXTRO ARABINOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 ANISYL) 5 PHENYL 2 (BETA DEXTRO ARABINOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 ANISYL) 5 PHENYL 2 (BETA DEXTRO GLUCOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 CHLOROPHENYL) 5 PHENYL 2 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 CHLOROPHENYL) 5 PHENYL 2 (2',3',5' TRI O ACETYL BETA DEXTRO ARABINOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 CHLOROPHENYL) 5 PHENYL 2 (BETA DEXTRO ARABINOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; 7 (4 CHLOROPHENYL) 5 PHENYL 2 (BETA DEXTRO GLUCOPYRANOSYLTHIO)PYRIDO [2,3 D] PYRIMIDIN 4 ONE; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; INDOMETACIN; PYRIDO[2,3 D]PYRIMIDINE DERIVATIVE; TRAMADOL; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; MALE; NONHUMAN; PAIN; PAW EDEMA; RAT;

EID: 79952031905     PISSN: None     EISSN: 0976044X     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. Feuer G, The metabolism and biological actions of coumarins. Prog. Med. Chem. 58,1973, 85-91.
2. Obaseki A O, Porter W R, 4-Hydroxycoumarin / 2- hydroxychromone tauto-merism: infrared spectra of 2-13C and 3-D labeled 4-hydroxycoumarin and its anion J. Heterocyclic Chem., 19, 1982, 385-90.
3. Yakout E M A, Ibrahim N M, Ghoneim Kh M, Mahran M R H, Reactions of 4-Hydroxycoumarin and 4- Hydroxyfurocoumarins with α,β-Unsaturated Nitriles. Mass Spectrometry of the New γ-Pyrano-α- pyran Derivatives J. Chem. Res. (S), 652, 1999, 2818-47.
4. Manolov I, Danchev N D, Synthesis, toxicological, and pharmacological assessment of some oximes and aldehyde condensation products of 4- hydroxycoumarin. Arch. Pharm. (Weinheim). 332, 1999, 243-48
5. Das Gupta A K, Chatterjee R M, Das, K R, A facile one-step synthesis of 4-hydroxycoumarin, Indian J. Chem. 20B, (1981) 511.
6. Martin J. T, Baker E. A, Bydre R J W, The fungitoxicities of plant furocoumarins; Ann. Appl. Biol., 57, 1966, 501.
7. Bingham J B, Meyer O O, Pohle F J, Studies on the hemorrhagic agent 3,3' methylenebis (4- hydroxycoumarin). I: its effect on the prothrombin and coagulation time of the blood of dogs and humans. Am J Med Sci, 202 1941, 563-78.
8. Patonay T, Litkei G, Bognar R, Erdei J, Miszti C, Antibacterial and Antifungal Activity of 4- Hydroxycoumarin Derivatives, Analogues of Novobiocin, Pharmazie, 39,1984, 86-91.
9. Yang B, Sutcliffe J, Dutton C J, 4-hydroxy coumarin derivatives., U. S. US 5985912, 1999.
10. Ali U. Shaikh A, Claudiu T S, Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin, Journal of Enzyme Inhibition and Medicinal Chemistry, 21, 2006, 741 - 748
11. Cingolani G M, Gualtrieri F, Pigini M, Notes. Researches in the Field of Antiviral Compounds. Mannich Bases of 3-Hydroxycoumarin, J. Med. Chem., 12, 1969, 531-532.
12. David L. Dreyer, Kenneth C. Jones, Leonard Jurd, Bruce C. Campbell, Feeding deterrency of some 4- hydroxycoumarins and related compounds: Relationship to host-plant resistance of alfalfa towards pea aphid (Acyrthosiphon pisum)., J. Chem., Ecol., 13, 925-30 (1987); C. A., 107, (1987) 20953.
13. Abortion effect of 3-(acetonylbenzyl)-4- hydroxycoumarin (warfarin) in mice, International J of Contraception 3, 1971, 279-283
14. Bariana D S, Coumarin derivatives as coronary vasodilators. J. Med. Chem., 13, 1970, 544-46.
15. Shah A, Naliapara Y, Sureja D, Motohashi N, Kawas M, Miskolci C, Szabo D, Molnar J, Biological activity of 6,12-dihydro-1-benzopyrano[3,4-b]- [1,4]benzothiazin-6-ones. Anticancer Res., 18 (4c), 1998, 61-3.
16. Yamato M, Jpn. Kokai. Takkyo Koho JP61, 215341,1986.; C. A., 106, (1987) 66807.
17. Tzeng C C, Lee K H, Chen Y L, Huang B R, U. S. US 5 962460,1999.; C. A., 131, (1999) 243173.
18. Bourinbaiar A S, U. S. US 5 811390,1998.; C. A., 129, (1998) 255529.
19. Kawano M,Chiba T, Akita Kogyo Koto Senmon Gakko Kenkyu Kiyo, 35, 64 (2000); C. A., 133, (2000) 232374.
20. Hariprasad V, Talele T T and Kulkarni V M, Crystal- Structure-Based Design and Synthesis of Novel Series of Non-peptidic Potential HIV-1 Protease Inhibitors. Pharm.Pharmcol. Commun. 4, 1998, 365-372.
21. Huang H C, Lai M W, Wang H R, Chung Y L, Hsieh L M,Chen C C, Antiproliferative effect of esculetin on vascular smooth muscle cells: possible roles of signal transduction pathways.Eur. J. Pharmacol., 237, 1995, 39-44.
22. Podbielkowska M, Kupidlowska E, Waleza M, Dobrzynska K, Louis S A, Keightley A, Zobel A M, Coumarins as Antimitotics., Int. J. Pharmacogen., 32, 1994, 262-273.
23. El-Gazzar A B A, Youssef M M, Youssef A M S, Abu-Hashem A A, Badria F A, Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities., Euro. J. of Med. Chem., 44, 2008, 609-624.
24. El-Gazzar A B A, El-Enany M A, Youssif M N, Synthesis, analgesic, anti-inflammatory, and antimicrobial activity of some novel pyrimido[4,5-b]quinolin-4- ones, Bioorg and Med. Chem., 16 (2008) 3261-3273.
25. El-Gazzar A B A, Hafez H N, Abbas H S, S- and Cnucleosidoquinazoline as new nucleoside analogs with potential analgesic and anti-inflammatory activity Euro. J. Med. Chem., 44, 2009, 4249-4258.
26. El-Gazzar A B A, Hafez H N, Nawwar G A, New acyclic nucleosides analogues as potential analgesic, antiinflammatory, anti-oxidant and anti-microbial derived from pyrimido[4,5-b]-quinolines., Euro. J. Med. Chem., 44, 2009, 1427-1436.
27. El-Gazzar A B A, Hafez H N, Synthesis and antitumor activity of substituted triazolo[4,3-a]pyrimidin-6- sulfonamide with an incorporated thiazolidinone moiety., Bioog. Med. Chem. Lett., 19, 2009, 4143-4147.
28. Hafez H N, El-Gazzar A B A, Synthesis of 4- substituted pyrido[2,3-d]-pyrimidin-4(1H)-one as analgesic and anti-inflammatory agents., Bioorg. Med. Chem. Lett., 19, 2009, 3392-3397.
29. Winter G A, Rislfy E A, Nuss G W, Proc. Soc. Exp. Biol. Med.111,1962, 544-547.
30. Armitage P, Statistical Methods in Medical Research, 1 Ed. Blackwell Scientific Publ., Oxford, London, 1971, 147.
31. Woolfe G, MacDonald A D, The evaluation of the analgesic action of pethidine hydrochloride (Demerol)., J. Pharmacol. Exp. Ther. 80,1944, 300-307.
32. Rajanna K C, Florence Solomon, Mir Moazzam Ali, Saiprakash P K., Kinetics and mechanism of Vilsmeier-Haack synthesis of 3-formyl chromones derived from o-hydroxy aryl alkyl ketones: A structure reactivity study, Tetrahedron, 52, 1996, 3669-3682
33. Amr A E, Abdulla M M, Synthesis and Antiinflammatory Activities of New Cyanopyrane Derivatives Fused with Steroidal Nuclei, Arch. Pharm. Chem. Life Sci. 339, 2006, 88-95.
34. Obukowics M G, Walseh D J, Salsgiver W J, Martin- Berger C L, Chinn K S, Duffin K L, Ras A, Needleman P, Novel, Selective Delta 6 or Delta 5 Fatty Acid Desaturase Inhibitors as Antiinflammatory Agents in Mice, J. Pharmacol. Exp. Ther. 287, 1998, 157-166.
35. Meng L, Mohan R, Kwok B H B, Elofssof M, Sin N, Crews C M, Proteasome Inhibitor and Antiinflammatory Activity., Proc. Natl. Acad. Sci. USA 96, 1999, 10403-10408.
36. Fathalla O M, Kassem E M M, Ibrahem N M, Kamel M M, Synthesis of some new quinazolin-4-one derivatives and evaluation of their antimicrobial and antiinflammatory effects., Acta Pol. Pharm. Drug Res. 65 (1), 2008, 11-20.
37. Eaton M, Common animal models for spasticity and pain., J. Rehabil Res. Dev. 40, 2003, 41-54.