Design and synthesis of some novel hydrazide, 1,2-dihydropyridine, chromene derivatives carrying biologically active sulfone moieties with potential anticancer activity

Mahmoud S Bashandy; Mansour S. Al-Said; Saleh I. Al-Qasoumi; Mostafa M. Ghorab

doi:10.1055/s-0031-1296238

Arzneimittelforschung, Table of Contents

Arzneimittelforschung 2011; 61(9): 521-526
DOI: 10.1055/s-0031-1296238

Antibiotics · Antimycotics · Antiparasitics · Antiviral Drugs · Chemotherapeutics · Cytostatics

Editio Cantor Verlag Aulendorf (Germany)

Design and synthesis of some novel hydrazide, 1,2-dihydropyridine, chromene derivatives carrying biologically active sulfone moieties with potential anticancer activity

Mahmoud S Bashandy

¹Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

,

Mansour S. Al-Said

²Medicinal, Aromatic and Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

,

Saleh I. Al-Qasoumi

³Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

,

Mostafa M. Ghorab

²Medicinal, Aromatic and Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, Riyadh, Saudi Arabia

⁴Department of Drug Radiation Research, National Center for Radiation Research and Technology, Nasr City, Cairo, Egypt

› Author Affiliations

Abstract

This paper describes the synthesis of some novel sulfones having biologically active hydrazides (4-9, 22, 23, 26 and 27), hydrazonoyl cyanide (24), 1,2-dihydro-pyridines (16-21), chromene (28) and benzochromene (29) moieties starting with 1-[4-(piperidin-1-ylsulfonyl)phenyl]-ethanone 1. The structures of the the newly synthesized compounds were confirmed by elemental analysis, IR, ¹H NMR and ¹³C NMR. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against breast cancer cell line (MCF7).

Key words

Anticancer activity - Breast cancer cell line - Chromene derivatives - 1,2-Dihydropyridine - Hydrazide derivatives - Sulfone derivatives

Full Text

References

References
1 El-Ezbawy SR, ALShaikh MA. Synthesis and antibacterial activity of some new pyridyl diarylsulfide and diarylsul-fones. Phosphorus Sulfur Silicon. 1990; 48: 111-6
2 Paul SH, Quyen-Quyen TD, David MW. Chemically enabled synthesis of 2-amino-4-heteroarylpyrimidines. Tetrahedron Lett. 2009; 50: 2552-4
3 Becker DP, Villamil CI, Barta TE, Bedell LJ, Boehm TL, De-Crescenzo GA et al. Synthesis and structure activity relationships of b- and α-piperidine sulphone hydroxamic acid matrix metalloproteinase inhibitors with oral antitumor efficacy. J Med Chem. 2005; 48: 6713-30
4 Zhang C, Lovering F, Behnke M, Zask A, Sandanayaka V, Sun L et al. Synthesis and activity of quinolinylmethyl ← α-sulfone piperidine hydroxamate inhibitors of TACE. Bioorg Med Chem Lett. 2009; 19: 3445-8
5 Arias LA, Arbelo D, Alzerreca A, Prieto JA. Synthesis of functionalized enamines from lithium alkyl phenyl sul-fones and N-carbo-tert-butoxy lactams. J Heterocyclic Chem. 2001; 38: 29-33
6 DasGupta S, Murumkar PR, Giridhar R, Yadav MR. Current perspective of TACE inhibitors. Bioorg Med Chem. 2009; 17: 444-59
7 Kamal A, Naseer M, Khan A, Reddy KS, Rohini K. Synthesis of a new class of 2-anilino substituted nicotinyl arylsulfo-nylhydrazides as potential anticancer and antibacterial agents. Bioorg Med Chem. 2007; 15: 1004-13
8 De R, Baltas M, Lamoral D, Bruyere C, Kiss R, Bedos F, Saf-fon N. Synthesis and anticancer activity evaluation of 2(4-alkoxyphenyl)-cyclopropyl hydrazides and triazolo phthal-azines. Bioorg Med Chem. 2010; 18: 2537-48
9 Bouget K, Aubin S, Delcros J, Arlot Y, Baudy M. Hydrazino-aza and N-aza-peptoids with therapeutic potential as anticancer agents. Bioorg Med Chem. 2003; 11: 4881-9
10 Zheng X, Cao J, Meng W, Qing F. Synthesis and anticancer effect of B-Ring trifluoromethylated flavonoids. Bioorg Med Chem Lett. 2003; 13: 3423-7
11 Payne SL, Rodriguez-Aristegui S, Bardos J, Cano C, Golding BT, Hard-castle IR et al. Mapping the ATP-binding domain of DNA-dependent protein kinase (DNA-PK) with coumarin and isocoumarin derived inhibitors. Bioorg Med Chem Lett. 2010; 20: 3649-53
12 Lacova M, Stankovicova H, Bohac A, Kotzianova B. Convenient Synthesis and Unusual Reactivity of 2-oxo-2H,5H-pyrano[3,2-c]chromenes. Tetrahedron. 2008; 64: 9646-53
13 Al-Said MS, Ghorab MM, Al-Qasoumi SI, El-Hossary EM, Noaman E. Synthesis and in vitro anticancer screening of some novel 4-[2-amino-3-cyano-4-substituted-5,6,7,8-tetrahydroquinolin-l-(4H)-yl]benzenesulfonamides. Eur J Med Chem. 2010; 45: 3011-8
14 Ghorab MM, Ismail ZH, Abdalla M. Synthesis and biological activities of some novel triazoloquinazolines and triazi-noquinazolines containing benzenesulfonamide moieties. Arzneimittelforschung. 2010; 60: 87-95
15 Al-Qasoumi SI, Al-Taweel AM, Alafeefy AM, Noaman E, Ghorab MM. Novel quinolines and pyrimido[4,5-b]quino-lines bearing biologically active sulfonamide moiety as a new class of antitumor agents. Eur J Med Chem. 2010; 45: 738-44
16 Skehan P, Storegng R, Scudiero D, Monks A, McMahon J, Vistica D et al. New colorimetric cytotoxicity assay for anticancer drug screening. J Natl Cancer Ins. 1990; 82: 1107-12
17 El-Kashef HS, Bayoumy BE, Aly TI. Selenium heterocycles I. Synthesis and antibacterial activity of some new 1,2,3-thia- and 1,2,3-selenadiazoles containing sulfonamides. Egypt J Pharm Sei. 1986; 27: 27-30
18 Zhou JF, Gong GX, Zhu FX, Zhi SJ. Microwave promoted one-pot synthesis of 3-(2′-amino-3′-cyano-4′-arylpyrid-6′-yl) coumarins. Chin Chem Lett. 2009; 20: 37-9
19 Volmajer J, Toplak R, Leban I, Marechal LMA. Synthesis of new iminocoumarins and their transformations into N-chloroandhydrazono compounds. Tetrahedron. 2005; 61: 7012-21