Skip to main content
SpringerLink
Log in

Synthesis of 1,5-benzothiazepine derivatives bearing 2-phenoxy-quinoline moiety via 1,3-diplolar cycloaddition reaction

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A series of 1,5-benzothiazepine derivatives were synthesized by the reaction of 1,5-benzothiazepine containing 2-phenoxy-quinoline with benzohydroximinoyl chlorides and hydrazonoyl chlorides at room temperature. The structures of these novel compounds were confirmed by spectrum, elemental, and X-ray crystallographic analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Jiang L, Wan X, Xu H, Bian J, Han W, Zhu K et al (2007) Effect of diltiazem and lidocaine on arterial pressure or heart rate and the quality of extubation in patients undergoing uvulopalato-pharyngoplasty. J Med Coll PLA 22: 230–233. doi:10.1016/S1000-1948(07)60046-X

    Article  CAS  Google Scholar 

  2. Grandolini G, Perioli L, Ambrogi V (1999) Synthesis of some new 1,4-benzothiazine and 1,5-benzothiazepine tricyclic derivatives with structural analogy with TIBO and their screening for anti-HIV activity. Eur J Med Chem 34: 701–709. doi:10.1016/S0223-5234(99)00223-8

    Article  CAS  Google Scholar 

  3. Richard S (2005) Vascular effects of calcium channel antagonists: new evidence. Drugs 65: 1–10. doi:10.2165/00003495-200565002-00002

    Article  PubMed  CAS  Google Scholar 

  4. Pei YZ, Michael JL, Owen DJ et al (2003) Efficient syntheses of benzothiazepines as antagonists for the mitochondrial sodium-calcium exchanger: potential therapeutics for type II diabetes. J Org Chem 68: 92–103. doi:10.1021/jo020446t

    Article  PubMed  CAS  Google Scholar 

  5. Kumari N, Saini RK, Joshi YC (2007) Synthesis of novel derivative of 1,5-benzothiazepines from 1,3-diketones and their antibacterial activity. Orient J Chem 23: 731–734

    CAS  Google Scholar 

  6. Zhu S (2004) Canadian multicenter clentiazem angina trial. S Chin J Card Dis 10: 72

    Google Scholar 

  7. Bariwal JB, Upadhyay KD, Manvar AT, Trivedi JC, Singh JS, Jain KS, Shah AK (2008) 1,5-Benzothiazepine, a versatile pharmacophore: a review. Eur J Med Chem 43: 2279–2290. doi:10.1016/j.ejmech.2008.05.035

    Article  PubMed  CAS  Google Scholar 

  8. Campiani G, Fiorini I, De Filippis MP, Ciani SM et al (1996) Cardiovascular characterization of pyrrolo[2,1-d][1,5]benzothiazepine derivatives binding selectively to the peripheral-type benzodiazepine receptor (PBR): from Dual PBR affinity and calcium antagonist activity to novel and selective calcium entry blockers. J Med Chem 39: 2922–2938. doi:10.1021/jm960162z

    Article  PubMed  CAS  Google Scholar 

  9. Ambrogi V, Grandolini G, Perioli L, Giusti L, Lucacchini A, Martini C (1995) Studies on annulated 1,4-benzothiazines and l,5-benzothiazepines. IX. Imidazo[2,1-d] [1,5]benzothiazepines: synthesis and in vitro benzodiazepine receptor affinity. Eur J Med Chem 30: 429–437. doi:10.1016/0223-5234(96)88253-5

    Article  CAS  Google Scholar 

  10. Azad M, Munawar MA, Siddiqui HL (2007) Antimicrobial activity and synthesis of quinoline-based chalcones. J Appl Sci 7: 2485–2489

    Article  CAS  Google Scholar 

  11. Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC (2001) Synthesis and antibacterial evaluation of certain quinolone derivatives. J Med Chem 44: 2374–2377. doi:10.1021/jm0100335

    Article  PubMed  CAS  Google Scholar 

  12. Tseng CH, Tzeng CC, Yang CL, Lu PJ, Chen HL, Li HY, Chuang YC, Yang CN, Chen YL (2010) Synthesis and antiproliferative evaluation of certain indeno[1,2-c]quinoline derivatives. J Med Chem 53: 6164–6179. doi:10.1021/jm1005447

    Article  PubMed  CAS  Google Scholar 

  13. Colin WW, Jonathan AK, Anthony GB, John EB, Marlene FC, Simon LC, Yaman G, Howard K, Roger MP, Pamela LP (2001) Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents. J Med Chem 44: 3187–3194. doi:10.1021/jm010929+

    Article  Google Scholar 

  14. Zhang HZ, Kasibhatla S, Kuemmerle J, Kemnitzer W et al (2005) Discovery and structure–activity relationship of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers and potential anticancer agents. J Med Chem 48: 5215–5223. doi:10.1021/jm050292k

    Article  PubMed  CAS  Google Scholar 

  15. Sakamoto T, Cullen MD, Hartman TL, Watson KM et al (2007) Synthesis and anti-HIV activity of new metabolically stable alkenyldiarylmethane non-nucleoside reverse transcriptase inhibitors incorporating N-methoxy imidoyl halide and 1,2,4-oxadiazole systems. J Med Chem 50: 3314–3321. doi:10.1021/jm070236e

    Article  PubMed  CAS  Google Scholar 

  16. Frizler M, Lohr F, Furtmann N, Klas J, Gutschow M (2011) Structural optimization of azadipeptide nitriles strongly increases association rates and allows the development of selective cathepsin inhibitors. J Med Chem 54: 396–400. doi:10.1021/jm101272p

    Article  PubMed  CAS  Google Scholar 

  17. Catarzi D, Colotta V, Varano F, Calabri FR, Filacchioni G, Galli A, Costagli C, Carla V (2004) Synthesis and biological evaluation of analogues of 7-chloro-4,5-dihy dro-4-oxo-8-(1,2,4-triazol-4-yl)-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylic acid (TQX-173) as novel selective AMPA receptor antagonists. J Med Chem 47: 262–272. doi:10.1021/jm030906q

    Article  PubMed  CAS  Google Scholar 

  18. Naito Y, Akahoshi F, Takeda S, Okada T, Kajii M, Nishimura H, Sugiura M, Fukaya C, Kagitani Y (1996) Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia. J Med Chem 39: 3019–3029. doi:10.1021/jm9507993

    Article  PubMed  CAS  Google Scholar 

  19. Wadsworth HJ, Jenkins SM, Orlek BS, Cassidy F, Clark MSG, Brown F, Riley G J, Graves D, Hawkins J, Naylor CB (1992) Synthesis and muscarinic activities of quinuclidin-byltriazole and -tetrazole derivatives. J Med Chem 35: 1280–1290. doi:10.1021/jm00085a016

    Article  PubMed  CAS  Google Scholar 

  20. Burrell G, Evans JM, Hadley MS, Hicks F, Stemp G (1994) Benzopyran potassium channel activators related to cromakalim-heterocyclic amide replacements at position 4. Bioorg Med Chem Lett 4: 1285–1290. doi:10.1016/S0960-894X(01)80346-2

    Article  CAS  Google Scholar 

  21. Stephens W, Field L (1959) A seven-membered heterocycle from o-aminobenzenethiol and chalcone. J Org Chem 24: 1576. doi:10.1021/jo01092a610

    Article  CAS  Google Scholar 

  22. Pant S, Sharma P, Pant UC (2008) Synthesesand antimicrobial evaluation of 2-(2- Chlorophenyl)-4-(4-chlorophenyl/2-thienyl)-2,5-dihydro-8-substituted-1,5-benzothiazepines. Phosphorus Sulfur Silicon 183: 2974–2983. doi:10.1080/10426500802048920

    Article  CAS  Google Scholar 

  23. Lu YC, Jin S, Xing QY (1988) Theoretical conformation analysis of 1,5-benzodiazepines and benzothiazepinds. J Mol Struct (Theochem) 167: 253–267. doi:10.1016/0166-1280(88)80230-6

    Article  Google Scholar 

  24. Devi I, Baruah B, Bhuyan PJ (2006) α-cyclisation of tertiary amines: synthesis of some novel annelated quinolines via a three-component reaction under solvent-free conditions. Synlett 16: 2593–2596. doi:10.1055/s-2006-951477

    Google Scholar 

  25. Liu KC, Shelton BR, Howe RK (1980) A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors). J Org Chem 45: 3916–3918. doi:10.1021/jo01307a039

    Article  CAS  Google Scholar 

  26. Perrone MG, Santandrea E, Dell’Uomo N, Giannessi F, Milazzo FM, Sciarroni AF, Scilimati AF, Tortorella V (2005) Synthesis and biological evaluation of new clofibrate analogues as potential PPARa agonists. Eur J Med Chem 40: 143–154. doi:10.1016/j.ejmech.2004.09.018

    Article  PubMed  CAS  Google Scholar 

  27. Anderson WK, Jones AN (1984) Synthesis and evaluation of furan, thiophene, and azole bis[ (carbamoyloxy)methyl] derivatives as potential antineoplastic agents. J Med Chem 27: 1559–1565. doi:10.1021/jm00378a006

    Article  PubMed  CAS  Google Scholar 

  28. Xie ZF, Mo XX, Liu G, Liu FM (2008) Synthesis and crystal structure of 5-pyrazol-4,5-dihydropyrazoles derivatives. J Heterocycl Chem 45: 1485–1488. doi:10.1002/jhet.5570450539

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 310036, Zhejiang, People’s Republic of China

    Zhi-Qiang Dong, Fang-Ming Liu & Zai-Liang Yuan

  2. Zhejiang Transfar Co., Ltd., Hangzhou, 311215, Zhejiang, People’s Republic of China

    Feng Xu

Authors
  1. Zhi-Qiang Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fang-Ming Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Feng Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zai-Liang Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fang-Ming Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dong, ZQ., Liu, FM., Xu, F. et al. Synthesis of 1,5-benzothiazepine derivatives bearing 2-phenoxy-quinoline moiety via 1,3-diplolar cycloaddition reaction. Mol Divers 15, 963–970 (2011). https://doi.org/10.1007/s11030-011-9328-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-011-9328-z

Keywords

Search

Navigation