Synthesis and Caco-2 cell permeability of N-substituted anthranilamide esters as ADP inhibitor in platelets

详细信息    查看全文

• 作者：Sohee Kim ; Beom Soo Shin ; Eunsook Ma
• 关键词：Antiplatelet activity ; ADP inhibitor ; N ; Substituted anthranilamide ester ; Caco ; 2 cell ; Apparent permeability coefficients
• 刊名：Archives of Pharmacal Research
• 出版年：2015
• 出版时间：June 2015
• 年：2015
• 卷：38
• 期：6
• 页码：1147-1156
• 全文大小：792 KB
• 参考文献：Angiolillo, D.J., D.L. Bhatt, P.A. Gurbel, and L.A. Jennings. 2009. Advances in antiplatelet therapy: Agents in clinical development. American Journal of Cardiology 103: 40A-1A.PubMed View Article
  Anninos, H., G. Andrikopoulos, S. Pastromas, D. Sakellarich, G. Theodorakis, and P. Vardas. 2009. Triflusal: An old drug in modern antiplatelet therapy. Review of its action, use, safety and effectiveness. Hellenic Journal of Cardiology 50: 199-07.PubMed
  Antithrombotic triallist’s collaboration. 2002. Collaborative meta-analysis of randomised trials of antiplatelet therapy for prevention of death, myocardial infarction, and stroke in high risk patients. BMJ 324: 71-6.View Article
  Artursson, P., and J. Karlsson. 1991. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochemical and Biophysical Research Communication 175: 880-85.View Article
  Artursson, P., K. Palm, and K. Luthman. 1996. Caco-2 monolayers in experimental and theoretical predictions of drug transport. Advanced Drug Delivery Reviews 22: 67-4.View Article
  Bennett, J.S. 2001. Novel platelet inhibitors. Annual Review of Medicine 52: 161-84.PubMed View Article
  Berger, P.B. 1999. The thienopyridines in coronary artery disease. Current Cardiology Reports 1: 192-98.PubMed View Article
  Bhatt, D.L., and E.J. Topol. 2003. Scientific and therapeutic advances in antiplatelet therapy. Nature Reviews Drug Discovery 2: 15-8.PubMed View Article
  Born, G.V.R. 1962. Aggregation of blood platelets by adenosine diphosphate (ADP) and its reversal. Nature 194: 927-29.PubMed View Article
  Borne, R.F., R.L. Peden, I.W. Waters, M. Weiner, R. Jordan, and E.A. Coats. 1974. Anti-inflammatory activity of para-substituted N-benzenesulfonyl derivatives of anthranilic acid. Journal of Pharmaceutical Sciences 63: 615-17.PubMed View Article
  Caldwell, G.W., D.M. Richie, and J.A. Masucci. 2001. The new pre-preclinical paradigm: Compound optimization in early and late phase drug discovery. Current Topics in Medicinal Chemistry 1: 353-66.PubMed View Article
  Daniel, J.L., C. Dangelmaier, J. Jin, B. Ashby, J.B. Smith, and S.P. Kunapuli. 1998. Molecular basis for ADP induced platelet activation, I: Evidence for three distinct ADP receptors on human platelets. Journal of Biological Chemistry 273: 2024-029.PubMed View Article
  Davi, G., and C. PatRono. 2007. Platelet activation and atherothrombosis. New England Journal of Medicine 357: 2482-494.PubMed View Article
  Eisert, W.G. 2001. How to get from antiplatelet to antithrombotic treatment. American Journal of Therapeutics 8: 443-49.PubMed View Article
  Gan, L.-S., and D. Thakker. 1997. Applications of the Caco-2 model in the design and development of orally active drug elucidation of biochemical and physical barriers posed by the intestinal epithelium. Advanced Drug Delivery Reviews 23: 77-8.View Article
  He, X., M. Sugawara, Y. Takekuma, and K. Hiyazaki. 2004. Absorption of ester prodrugs in Caco-2 and rat intestine models. Antimicrobial Agents and Chemotherapy 48: 2604-609.PubMed Central PubMed View Article
  Ha-Duong, N.T., S. Dijols, A.-C. Macherey, J.A. Goldstein, P.M. Dansette, and D. Mansey. 2001. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40: 12112-2122.PubMed View Article
  Ho, P.M., T.M. Maddox, L. Wang, S.D. Fihn, R.L. Jesse, E.D. Peterson, and J.S. Rumsfeld. 2009. Risk of adverse outcomes associated with concomitant use of clopidogrel and proton pump inhibitors following acute coronary syndrome. Journal of the American Medical Association 301: 937-44.PubMed View Article
  Hsieh, P.W., S.Z. Chiang, C.C. Wu, Y.C. Lo, Y.T. Shih, and Y.C. Wu. 2008. Synthesis and anti-platelet evaluation of 2-benzoylaminobenzoate analogs. Bioorganic & Medicinal Chemistry 16: 5803-814.View Article
  Hsieh, P.W., T.L. Hwang, C.C. Wu, S.Z. Chiang, C.L. Wu, and Y.C. Wu. 2007. The evaluation and structure-activity relationships of 2-benzoylaminobenzoic esters and their analogues as anti-inflammatory and anti-platelet aggregation agents. Bioorganic & Medicinal Chemistry Letters 17: 1812-817.View Article
  Iwasa, Y., T. Iwasa, K. Matsui, T. Yoshimura, N. Tanaka, and K. Miyazaki. 1986. Anti-platelet action of an anti-allergic agent, N-(3-4-dimethoxycinnamoyl)anthranilic acid (Tranilast). European Journal of Pharmacology 120: 231-34.PubMed View Article
  Jackson, S.P., and S.M. Schoenwaelder. 2003. Antiplatelet therapy in search of the ‘magic bullet- Nature Reviews Drug Discovery 2: 775-89.PubMed View Article
  Kunapuli, S.D. 1998. Multiple P2 receptor subtypes on platelets: A new interpretation of their function. Trends in Pharmacological Sciences 19: 391-94.PubMed View Article
  Lim, J.K., W.S. Woo, K.R. Lee, and E. Ma. 1994. Synthesis of melandrin derivatives. Yakhak Hoeji 38: 281-85.
  Liu, F.-C., C.-H. Liao, Y.-E. C
• 作者单位：Sohee Kim (1)
  Beom Soo Shin (1)
  Eunsook Ma (1)
  
  1. College of Pharmacy, Catholic University of Daegu, 712-702, Hayangro 13-13, Gyeongsan, 712-702, Korea
  
• 刊物主题：Pharmacy; Pharmacology/Toxicology;
• 出版者：Springer Netherlands
• ISSN：1976-3786

文摘

Twelve N-substituted anthranilamide esters (1-strong class="EmphasisTypeBold">5, 8, 9, 12, 13, and 15-strong class="EmphasisTypeBold">17) were synthesized and evaluated for their ability to inhibit the in vitro aggregation by washed human platelets induced by adenosine 5-diphosphate (10?μM). The antiplatelet activity of dl-n-butyl 5-hydroxy-N-(2-phenoxypropionyl)anthranilate (9, IC50?=?10.5?μM) was most active among the tested compounds and ethyl ester 8 (IC50?=?11.2?μM) showed the second most activity. dl-Ethyl and dl-n-butyl 5-(p-toluenesulfonyloxy)-N-(2-phenoxypropionyl)anthranilate (12, IC50?=?13.1?μM and 13, IC50?=?14.0?μM), dl-methyl N-(2-phenoxybutyryl)anthranilate (2, IC50?=?12.7?μM), dl-N-(2-phenoxypropionyl)anthranilic acid (5, IC50?=?13.7?μM) displayed lower antiplatelet activity than 8 and 9. Compound 5 was more active than methyl ester prodrug 1. n-Butyl 5-hydroxy-N-(4-acetoxybenzoyl)anthranilate (15, IC50?=?28.3?μM) showed moderate activity. Compounds 1 (IC50?=?42.8?μM), 4 (IC50?=?56.7?μM), 16 (IC50?=?51.0?μM), and 17 (IC50?=?49.8?μM) exhibited low antiplatelet activity. Methyl N-phenoxyacetylanthranilate (3, IC50?=?78.0?μM) showed the lowest antiplatelet activity. The compounds with branched alkyl chain (2 and 5) were more active than compounds with straight chain (3 and 4). The apparent permeability coefficient (Papp, cm/s) values of compounds 2 and 9 were determined as 45.34?±?4.67 and 33.17?±?5.15?×?10??cm/s by Caco-2 cell permeability assay.