Stereoselective Synthesis of (Z)-1-Benzhydryl-4-cinnamylpiperazines via the Wittig Reaction

REFERENCES

• Todorovic , A. ; Luevano , H. C. A review of melanocortin receptor small molecule ligands . Peptides 2005 , 26 , 2026 – 2036 .
   PubMed Web of Science ®Google Scholar
• Kundu , B. Solid-phase strategies for the design and synthesis of heterocyclic molecules of medicinal interest . Curr. Opin. Drug Discov. Develop. 2003 , 6 , 815 – 826 .
   PubMed Web of Science ®Google Scholar
• Atherden , L. H. Bentley and Driver's Text Book of Pharmaceutical Chemistry, , 8th ed. ; Oxford Medicinal Publication : Oxford , UK , 2004 ; pp. 372 – 377 and 204 – 205 .
   Google Scholar
• Beckett , A. H. ; Stenlake , J. B. Practical Pharmaceutical Chemistry, , 4th ed. ; CBS Publishers 2003 .
   Google Scholar
• Andrejus , K. Essentials of Medicinal Chemistry, 2nd ed. ; Wiley-Interscience , 1988 ; p. 601 .
   Google Scholar
• Phillips , O. A. ; Udo , E. E. ; Samuel , S. M. Synthesis and structure–antibacterial activity of triazolyl oxazolidinones containing long-chain acyl moiety . Eur. J. Med. Chem. 2008 , 43 , 1095 – 1104 .
   PubMed Web of Science ®Google Scholar
• Foroumadi , A. ; Emami , S. ; Mansouri , S. ; Javidnia , A. ; Saeid-Adeli , N. ; Shirazi , F. H. ; Shafiee , A. Synthesis and antibacterial activity of levofloxacin derivatives with certain bulky residues on piperazine ring . Eur. J. Med. Chem. 2007 , 42 , 985 – 992 .
   PubMed Web of Science ®Google Scholar
• Lohray , B. B. ; Lohray , V. B. ; Srivastava , B. K. ; Gupta , S. ; Solanki , M. ; Pandya , P. ; Kapadnis , P. Novel 4-N-substituted aryl pent-2-ene-1,4-dione derivatives of piperazinyloxazolidinones as antibacterials . Bioorg. Med. Chem. Lett. 2006 , 16 , 1557 – 1561 .
   PubMed Web of Science ®Google Scholar
• Foroumadi , A. ; Ghodsi , S. ; Emami , S. ; Najjari , S. ; Samadi , N. ; Faramarzi , M. A. ; Beikmohammadi , L. ; Shirazi , F. H. ; Shafiee , A. Synthesis and antibacterial activity of new fluoroquinolone containing a substituted N-(phenethyl)piperazine moiety. Bioorg. Med. Chem. Lett. 2006, 16, 3499–3503.
   PubMed Web of Science ®Google Scholar
• Watkins , W. J. ; Chong , L. ; Cho , A. ; Hilgenkamp , R. ; Ludwikow , M. ; Garizi , N. ; Iqbal , N. ; Barnard , J. ; Singh , R.. ; Madsen , D. ; Lolans , K. ; Lomovskaya , O. ; Oza , U. ; Kumaraswamy , P. ; Blecken , A. ; Bai , S. ; Loury , D. J. ; Griffitha , D. C. ; Dudley , M. N. Quinazolinone fungal efflux pump inhibitors, part 3: (N-Methyl) piperazine variants and pharmacokinetic optimization . Bioorg. Med. Chem. Lett. 2007 , 17 , 2802 – 2806 .
   PubMed Web of Science ®Google Scholar
• Upadhayaya , R. S. ; Sinha , N. ; Jain , S. ; Kishore , N. ; Chandra , R. ; Arora , S. K. Optically active antifungal azoles: Synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol . Bioorg. Med. Chem. 2004 , 12 , 2225 – 2238 .
   PubMed Web of Science ®Google Scholar
• Rokosz , L. L. ; Huang , C. Y. ; Reader , J. C. ; Stauffer , T. M. ; Chelsky , D. ; Sigal , N. H. ; Ganguly , A. K. ; Baldwin , J. J. Surfing the piperazine core of tricyclic farnesyltransferase inhibitors . Bioorg. Med. Chem. Lett. 2005 , 15 , 5537 – 5543 .
   PubMed Web of Science ®Google Scholar
• Chen , J. J. ; Lu , M. ; Jing , Y. K. ; Dong , J. H. The synthesis of l-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells . Bioorg. Med. Chem. 2006 , 14 , 6539 – 6547 .
   PubMed Web of Science ®Google Scholar
• Shami , P. J. ; Saavedra , J. E. ; Bonifant , C. L. ; Chu , J. X. ; Udupi , V. ; Malaviya , S. ; Carr , B. I. ; Kar , S. ; Wang , M. F. ; Jia , L. ; Ji , X. H. ; Keefer , L. K. Antitumor activity of JS-K [O 2-(2,4-dinitrophenyl)1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O 2-aryl diazeniumdiolates in vitro and in vivo . J. Med. Chem. 2006 , 49 , 4356 – 4366 .
   PubMed Web of Science ®Google Scholar
• Mayence , A. ; Eynde , J. J. V. ; LeCour Jr. , L. ; Walker , L. A. ; Tekwani , B. L. ; Huang , T. L. Jr. Piperazine-linked bisbenzamidines: A novel class of antileishmanial agents . Eur. J. Med. Chem. 2004 , 39 , 547 – 553 .
   PubMed Web of Science ®Google Scholar
• Cunico , W. ; Gomes , C. R. B. ; Moreth , M. ; Manhanini , D. P. ; Figueiredo , I. H. ; Penido , C. ; Henriques , M. G. M. O. ; Varotti , F. P. ; Krettli , A. U. Synthesis and antimalerial activity of hydroxyethylpiperazine derivatives . Eur. J. Med. Chem. 2009 , 44 , 1363 – 1368 .
   PubMed Web of Science ®Google Scholar
• Smits , R. A. ; Lim , H. D. ; Hanzer , A. ; Zuiderveld , O. P. ; Guaita , E. ; Adami , M. ; Coruzzi , G. ; Leurs , R. ; Esch , I. J. P. Fragment based design of new H4 receptor−ligands with anti-inflammatory properties in vivo . J. Med. Chem. 2008 , 51 , 2457 – 2467 .
   PubMed Web of Science ®Google Scholar
• Penjišević , J. ; Šukalović , V. ; Andrić , D. ; Kostić-Rajačić , S. ; Šoškić , V. ; Roglić , G. 1-Cinnamyl-4-(2-methoxyphenyl) piperazines: Synthesis, binding properties, and docking to dopamine (D2) and serotonin (5-HT1A) receptors . Arch. Pharm. Chem. Life Sci. 2007 , 340 , 456 – 465 .
   PubMed Web of Science ®Google Scholar
• Becker , O. M. ; Dhanoa , D. S. ; Marantz , Y. ; Chen , D. ; Shacham , S. ; Cheruku , S. ; Heifetz , A. ; Mohanty , P. ; Fichman , M. ; Sharadendu , A. ; Nudelman , R. ; Kauffman , M. ; Noiman , S. An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment of anxiety and depression . J. Med. Chem. 2006 , 49 , 3116 – 3135 .
   PubMed Web of Science ®Google Scholar
• (a) Vacca , J. P. ; Dorsey , B. D. ; Schleif , W. A. ; Levine , R. B. ; McDaniel , S. L. ; Darke , P. L. ; Zugay , J. ; Quintero , J. C. ; Blahy , O. M. An orally bioavailable human immunodeficiency virus type 1 protease inhibitor. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4096–4100; (b) Vacca , J. P. ; Dorsey , B. D. ; Schleif , W. A. ; Levine , R. B. ; McDaniel , S. L. ; Darke , P. L. ; Zugay , J. The design of a potent and orally bioavailable HIV protease inhibitor. J. Med. Chem. 1994, 37, 3443–3451; (c) Askin , D. ; Eng , K. K. ; Rossen , K. ; Purick , R. M. ; Wells , K. M. ; Volante , R. P. ; Reider , P. J. Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate: Synthesis of the orally active HIV-1 protease inhibitor L-735,524. Tetrahedron Lett. 1994, 35, 673–676; (d) Rossen , K. ; Weissman , S. A. ; Sagar , J. ; Reamer , R. A. ; Askin , D. A. ; Volante , R. P. ; Reider , P. J. Asymmetric hydrogenation of tetrahydropyrazines: Synthesis of (S)-piperazine-2-tert-butylcarboxamide, an intermediate in the preparation of the HIV protease inhibitor indinavir. Tetrahedron Lett. 1995, 36, 6419–6422.
   PubMed Web of Science ®Google Scholar
• Kerns , R. J. ; Rybak , M. J. ; Kaatz , G. W. ; Vaka , F. ; Cha , R. ; Grucz , R. G. ; Diwadkar , V. U. Structural features of piperazinyl-linked ciprofloxacin dimers required for activity against drug-resistant strains of Staphylococcus aureus . Bioorg. Med. Chem. Lett. 2003 , 13 , 2109 – 2112 .
   PubMed Web of Science ®Google Scholar
• Lee , P. H. ; McNutt , R. W. ; Chang , K. J. A nonpeptidic delta opioid receptor agonist, BW373U86, attenuates the development and expression of morphine abstinence precipitated by naloxone in rat . J. Pharmacol. Exp. Ther. 1993 , 267 , 883 – 887 .
   PubMed Web of Science ®Google Scholar
• Ohtaka , H. ; Tsukamoto , G. V. Quantitative structure–activity relationships of 1-benzyl-4-diphenylmethylpiperazine derivatives for cerebral vasodilating activity . Chem. Pharm. Bull. 1987 , 35 , 4117 – 4123 .
   PubMedGoogle Scholar
• Paton , D. M. ; Webster , D. R. Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines) . Clin. Pharmacokinet. 1985 , 10 , 477 – 497 .
   PubMed Web of Science ®Google Scholar
• (a) Cignarella , G. ; Testa , E. V. J. Synthesis of 2,6-alkylpiperazine derivatives structurally related to cinnarizine . Med. Chem. 1968 , 11 , 612 – 615 ; (b) Serge , A. A. Process for the preparation of 1-transcinnamyl-4-diphenylmethylpiperazine. C.A. Patent 942306, 1974 ; (c) Younes , S. ; Baziard-Mouysset , G. ; de Saqui-Sannes , G. ; Stigliani , J. L. ; Payard , M. ; Bonnafous , R. Synthesis and pharmacological study of new calcium antagonists, analogues of cinnarizine and flunarizine . Eur. J. Med. Chem. 1993 , 28 , 943 – 948 .
   Web of Science ®Google Scholar
• (a) Ananda Kumar , C. S. ; Benaka Prasad , S. B. ; Vinaya , K. ; Chandrappa , S. ; Thimmegowda , N. R. ; Sunil Kumar , Y. C. ; Sanjay , S. ; Rangappa , K. S. Synthesis and in vitro antiproliferative activity of novel 1-benzhydrylpiperazine derivatives against human cancer cell lines . Eur. J. Med Chem. 2009 , 44 , 1223 ; (b) Gubert , S. ; Braso , M. A. ; Sacristan , A. ; Ortiz , J. A. Synthesis of some N-benzhydrylpiperazine derivatives as calcium antagonists . Arzneimittel-Forschung 1987 , 37 , 1103 .
   PubMed Web of Science ®Google Scholar
• Maryanoff , B. E. ; Reitz , A. B. ; Mutter , M. S. ; Whittle , R. R. ; Olofson , R. A. Stereochemistry and mechanism of the Wittig reaction. Diasteromeric reaction intermediates and analysis of the reaction course . J. Am. Chem. Soc. 1986 , 108 , 7664 – 7678 .
   PubMed Web of Science ®Google Scholar
• (a) Schlosser , M. ; Christmann , K. F. Olefinierungen mit Phosphor-Yliden, I: Mechanismus und Stereochemie der Wittig-Reaktion . Liebigs Ann. Chem. 1967 , 708 , 1 ; (b) Schlosser , M. ; Muller , G. ; Christmann , K. F. cis-Selective olefin syntheses . Angew. Chem. Int. Ed. Engl. 1966 , 5 , 667 .
   Google Scholar
• Roberti , M. ; Pizzirani , D. ; Simoni , D. ; Rondanin , R. ; Baruchello , R. ; Bonora , C. ; Buscemi , F. ; Grimaudo , S. ; Tolomeo , M. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents . J. Med. Chem. 2003 , 46 , 3546 – 3554 .
   PubMed Web of Science ®Google Scholar
• (a) Weston , A. W. ; Hamlin Jr. , K. E. Preparation of Piperazine Derivatives. U.S. Patent 2861072, Nov. 18, 1958 ; (b) Morren , H. G. ; Trolin , S. ; Denayer , R. ; Grivsky , E. ; Maricq , J. Nouvelles substances antihistaminiques à action prolongée: les 1–4 bis (aralcoyl) pipérazines . Bull. Soc. Chim. Belg. 1951 , 60 , 282 – 295 .
   Google Scholar
• Alonso , F. ; Riente , P. ; Yus , M. Synthesis of resveratrol, DMU-212 and analogues through a novel Wittig-type olefination promoted by nickel nanoparticles . Tetrahedron Lett. 2009 , 50 , 3070 – 3073 .
   Web of Science ®Google Scholar