New approaches for the synthesis of pyrazole, thiophene, thieno[2,3-b]pyridine, and thiazole derivatives together with their anti-tumor evaluations

Medicinal Chemistry Research

Volumn 23, Issue 2, 2014, Pages 564-579

  Mohareb, Rafat M ^a   Abdallah, Amira E M ^b   Abdelaziz, Mahmoud A ^c,d  

^a CAIRO UNIVERSITY   (Egypt)

^b Helwan University   (Egypt)

^c Al Ghad International Colleges for Applied Medical Sciences   (Saudi Arabia)

^d Modern Academy for Engineering and Technology in Maadi   (Egypt)

Author keywords

Anti tumor; Pyrazole; Thiazole; Thieno 2,3 b pyridine; Thiophene

Indexed keywords

4 AMINO 5 BENZOYL N (4 (5 AMINO 3 HYDROXY 1H PYRAZOL 1 YL) 3 ETHOXYCARBONYLTHIOPHEN 2 YL) 2 (PHENYLAMINO)THIOPHENE 3 CARBOXAMIDE; 5 ACETYL 4 AMINO N (4 (5 AMINO 3 HYDROXY 1H PYRAZOL 1 YL) 3 CYANOTHIOPHEN 2 YL) 2 (PHENYLAMINO)THIOPHENE 3 CARBOXAMIDE; ACETYL CHLORIDE; ANTINEOPLASTIC AGENT; CYANOACETYLHYDRAZINE; DOXORUBICIN; ETHYL 2 ALPHA (P CHLOROPHENYLHYDRAZONO) 2 CYANOACETAMIDO) 4 (5 AMINO 3 HYDROXY 1H PYRAZOL 1 YL)THIOPHENE 3 CARBOXYLATE; N (4 (5 AMINO 3 HYDROXY 1H PYRAZOL 1 YL) 3 CYANOTHIOPHEN 2 YL) ALPHA (P CHLOROPHENYLHYDRAZONO) 2 CYANOACETAMIDE; PYRAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; THIENO[2,3 B]PYRIDINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CELL STRAIN MCF 7; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; LUNG NON SMALL CELL CANCER; MOLECULAR MODEL; TUMOR CELL LINE;

EID: 84893768437     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0664-7     Document Type: Article

References (25)

1. Abadi AH, Abdel Haleem Eissa Hassan A, Hassan GS (2003) Chem Pharm Bul 51:838-844
2. Al-Said MS, Bashandy MS, Al-gasoumi SI, Ghorab MM (2011) Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives. Eur J Med Chem 46(1):137-141
3. Bondock S, Fadaly W, Metwally MA (2010) Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem 45(9):3692-3701
4. Brasca MG, Albanese C, Amici R, Ballinari D, Corti L, Croci V, Fancelli D, Fiorentini F, Nesi M, Orsini P, Orzi F, Pastori W, Perrone E, Pesenti E, Pevarello P, Riccardi-Sirtori F, Roletto F, Roussel P, Varasi M, Vulpetti A, Mercurio C (2007) 6-Substituted pyrrolo[3,4-c]pyrazoles: an improved class of CDK2 inhibitors. Chem Med Chem 2:841-852
5. Cho N, Kamaura M, Yogo T, Imoto H (2009) PCT Int Appl WO 2009139340
6. Dugi K, Mark M, Himmelsbach F (2009) PCT Int Appl WO 2009022009
7. Elguero J, Goya P, Jagerovic N, Silva AMS (2002) In: Attanasi OA, Spinelli D (eds) Targets in heterocyclic systems, 6th edn. Società Chimica Italiana, Roma, pp 52-98
8. Fadda AA, Abdel-Latif E, El-Mekawy RE (2009) Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives. Eur J Med Chem 44(3):1250-1256
9. Gouda MA, Berghot MA, Abd El-Ghani GE, khalil AM (2010) Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. Eur J Med Chem 45(4):1338-1345
10. Insuasty B, Tigreros A, Orozco F, Quiroga J, Abonia R, Nogueras M, Khalil AM, Berghot MA, Gouda MA (2009) Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Eur J Med Chem 44(11):4434-4440
11. Labbozzetta M, Baruchello R, Marchetti P, Gueli MC, Poma P, Notarbartolo M, Simoni D, D'Alessandro N (2009) Lack of nucleophilic addition in the isoxazole and pyrazole diketone modified analogs of curcumin; implications for their antitumor and chemosensitizing activities. Chem Biol Interact 181:29-36
12. Ludwig S, Planz O, Sedlacek HH, Pleschka S (2004) PCT Int Appl WO12
13. Hubbard SR, Till JH (2000) Rev Biochem 69(373):2004085682
14. Michaelides MR (2010) PCT Int Appl WO 2010065825
15. Momose Y, Maekawa T, Odaka H, Kimura H (2001) PCT Int Appl WO 2001038325
16. Perchellet EM, Ward MM, Skaltsounis AL, Kostakis IK, Pouli N, Marakos P, Perchellet JP (2006) Antiproliferative and proapoptotic activities of pyranoxanthenones, pyranothioxanthenones, and their pyrazole-fused derivatives in HL-60 cells. Anticancer Res 26:2791-2804
17. Pevarello P, Brasca MG, Amici R, Orsini P, Traquandi G, Corti L, Piutti C, Sansonna P, Villa M, Pierce BS, Pulici M, Giordano P, Martina K, Fritzen EL, Nugent RA, Casale E, Cameron A, Ciomei M, Roletto F, Isacchi A, Fogliatto G, Pesenti E, Pastori W, Marsiglio A, Leach KL, Clare PM, Fiorentini F, Varasi M, Vulpetti A, Warpehoski MA (2004) 3-Aminopyrazole inhibitors of CDK2/cyclin A as antitumor agents. 1. Lead finding. J Med Chem 47:3367-3380
18. Pevarello P, Fancelli D, Vulpetti A, Amici R, Villa M, Pittalà V, Vianello P, Cameron A, Ciomei M, Mercurio C, Bischoff JR, Roletto F, Varasi M, Brasca MG (2006) 3-Amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: a new class of CDK2 inhibitors. Bioorg Med Chem Lett 16:1084-1090
19. Regan J, Breitfelder S, Cirillo P, Gilmore T, Graham AG, Hickey E, Klaus B, Madwed J, Moriak M, Moss N, Pargellis C, Pav S, Proto A, Swinamer A, Tong L, Torcellini C (2002) Pyrazole urea-based inhibitors of p38 MAP kinase: from lead compound to clinical candidate. J Med Chem 45:2994-3008
20. Rida SM, Saudi MNS, Youssef AM, Halim MA (2009) Synthesis and biological evaluation of the pyrazole class of cyclooxygenase-2-inhibitors. Lett Org Chem 6:282-288
21. Sanchez A, Cobo J (2010) Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H- pyrazole derivatives as potential antitumor agents. Bioorg Med Chem 18:4965-4974
22. Sunil Kumar YC, Sadashiva MP, Rangappa KS (2007) An efficient synthesis of 2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)morpholine: a potent M1 selective muscarinic agonist. Tetrahedron Lett 48:4565-4568
23. Szabo G, Fischer J, Kis-Varga A, Gyires K (2008) New celecoxib derivatives as anti-inflammatory agents. J Med Chem 51:142-147
24. Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wachi M, Yamagishi J (2004) Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring. Bioorg Med Chem 12:5515-5524
25. Tanitame A, Oyamada Y, Ofuji K, Terauchi H, Kawasaki M, Wachi M, Yamagishi J (2005) Synthesis and antibacterial activity of a novel series of DNA gyrase inhibitors: 5-[(E)-2-arylvinyl]pyrazoles. Bioorg Med Chem Lett 15:4299-4303