\(N\)-Polybenzylated alicyclic 1,2-diamines: cytotoxicity and G1 phase arrest in cancer cell line

Ferlay J, Shin H-R, Bray F, Forman D, Mathers C, Maxwell Parkin D (2010) Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. Int J Cancer 127:2893–2917. doi: 10.1002/ijc.25516 PubMedCrossRefGoogle Scholar

Jemal A, Bray F, Center MM, Ferlay J, Ward E, Forman D (2011) Global cancer statistics. CA Cancer J Clin 61:69–90. doi: 10.3322/caac.20107 PubMedCrossRefGoogle Scholar

Lucet D, Le Gall T, Mioskowski C (1998) The chemistry of vicinal diamines. Angew Chem Int Ed Engl 37:2580–2647. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L

Michalson ET, Szmuszkovicz J (1989) Medicinal agents incorporating the 1,2-diamine functionality. Prog Drug Res 33:135–149. doi: 10.1007/978-3-0348-9146-2_6 PubMedCrossRefGoogle Scholar

Szmuszkovicz J, VonVoigtlander PF, Kane MP (1981) A new nontricyclic antidepressant agent. Synthesis and activity of \(N\)-[trans-2-(dimethy1amino)cyclopenty1]-\(N\)-(3,4-dichloro- phenyl)propanamide and related compounds. J Med Chem 24:1230–1236. doi: 10.1021/jm00142a020

Zubovics Z, Toldy L, Varrò A, Rabloczky G, Kürthy M, Dvortsàk P, Jerkovich G, Tomori E (1986) Synthesis and antiarrhythmic activity of \(N\)-arylalkylenediamines. Eur J Med Chem 21:370–378Google Scholar

Musa MA, Khan MO, Aspedon A, Cooperwood JS (2010) Synthesis and antimicrobial activity of N,N-bis(2-hydroxylbenzyl)-1,2-ethanediamine derivatives. Lett Drug Des Discov 7:165–170. doi: 10.2174/157018010790596678

Leal SM, Amado DF, Kouznetsov VV, Escobar P (2013) In vitro antileishmanial, trypanocidal, and mammalian cell activities of diverse \(N\),\(N^{\prime }\)-dihetaryl substituted diamines and related compounds. Sci Pharm 81:43–55. doi: 10.3797/scipharm.1205-14

Rebollo O, Del Olmo E, Ruiz G, López-Pérez JL, Giménez A, San Feliciano A (2008) Leishmanicidal and trypanocidal activities of 2-aminocyclohexanol and 1,2-cyclohexanediamine derivatives. Bioorg Med Chem Lett 18:184–187. doi: 10.1016/j.bmcl.2007.10.102 PubMedCrossRefGoogle Scholar

Rosenberg B, VanCamp L, Trosko JE, Mansour VH (1969) Platinum compounds: a new class of potent antitumour agents. Nature 222:385–386. doi: 10.1038/222385a0 PubMedCrossRefGoogle Scholar

Reedijk J (1996) Improved understanding in platinium antitumour chemistry. Chem Commun 801–806: doi: 10.1039/CC9960000801

Gust R, Burgemeister T, Mannschreck A, Schoenenberger H (1990) Aqua[1-(2,6-dichloro-4-hydroxyphenyl)-2-phenylethylenediamine](sulfato)platinum-(II) complexes with variable substituents in the 2-phenyl ring. 1. Synthesis and antitumor and estrogenic properties. J Med Chem 33:2535–2544. doi: 10.1021/jm00171a031 PubMedCrossRefGoogle Scholar

Kelland LR, Abel G, McKeage MJ, Jones M, Goddard PM, Valenti M, Murrer BA, Harrap KR (1993) Preclinical antitumor evaluation of bis-acetato-ammine-dichloro-cyclohexylamine platinum(IV): an orally active platinum drug. Cancer Res 53:2581–2586PubMedGoogle Scholar

Brunner H, Hankofer P, Holzinger U, Treittinger B, Schönenberger H (1990) Synthesis and antitumor activity of platinum(II) complexes containing substituted ethylenediamine ligands. Eur J Med Chem 25:35–44. doi: 10.1016/0223-5234(90)90162-V CrossRefGoogle Scholar

Brunner H, Hankoferm P, Holzinger U, Treittinger B (1990) Synthesis and antitumor activity of Pt(II) complexes of benzyl-1,2-diaminoethane ligands. Chem Ber 123:1029–1038. doi: 10.1002/cber.19901230515 CrossRefGoogle Scholar

Kim D-K, Kim Y-W, Kim H-T, Kim KH (1996) Synthesis and in vitro cytotoxicity of cis-dichloro[(\(2S,3R,4S\))-2-aminomethyl-3,4-(\(O\)-isopropylidene)dihydroxy- or -3,4-dihydro- xypyrrolidine]platinum(II). Bioorg Med Chem Lett 6:643–646. doi: 10.1016/0960-894X(96)00088-1

Khokhar AR, Al-Baker S, Shamsuddin S, Siddik ZH (1997) Chemical and biological studies on a series of novel (trans-(1R,2R)-, trans-(1S,2S)-, and cis-1,2-diaminocyclohexane)platinum(IV) carboxylate complexes. J Med Chem 40:112–116. doi: 10.1021/jm960587l PubMedCrossRefGoogle Scholar

McRipley RJ, Burns-Horwitz PE, Czerniak PM, Diamond RJ, Diamond MA, Miller JLD, Page RJ, Dexter DL, Chen S-F, Sun J-H, Behrens CH, Seitz SP, Gross JL (1994) Efficacy of DMP 840: a novel bis-naphthalimide cytotoxic agent with human solid tumor xenograft selectivity. Cancer Research 54:159–164PubMedGoogle Scholar

Cherney RJ, Swartz SG, Patten AD, Akamike E, Sun J-H, Kaltenbach RF III, Seitz SP, Behrens CH, Getahun Z, Trainor GL, Vavala M, Kirshenbaum MR, Papp LM, Stafford MP, Czerniak PM, Diamond RJ, McRipley RJ, Page RJ, Gross JL (1997) The synthesis and antitumor evaluation of unsymmetrical bis-imides. Bioorg Med Chem Lett 7:163–168. doi: 10.1016/S0960-894X(96)00591-4 CrossRefGoogle Scholar

Kulanthaivel P, Hallock YF, Boros C, Hamilton SM, Janzen WP, Ballas LM, Loomis CR, Jiang JB, Katz B (1993) Balanol: a novel and potent inbibitor of protein kinase C from the fungus Verticillium balanoides. J Am Chem Soc 115:6452–6453. doi: 10.1021/ja00067a087 CrossRefGoogle Scholar

Hoffmann T (1998) Characterization of the chemical structure of novel colored Maillard reaction products from furan-2-carboxaldehyde and amino acids. J Agric Food Chem 46:932–940. doi: 10.1021/jf970732j

Li S-W, Batey RA (2007) Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/ electrocyclization process. Chem Commun 36:3759–3761. doi: 10.1039/b709337n

Liu J, Yu J, Zhu M, Li J, Zheng X, Wang L (2013) Novel role of p-toluenesulfonamide in the preparation of 4,5-diaminocyclopent-2-enone. Synthesis 45:2165–2170. doi: 10.1055/s-0033-1339180 CrossRefGoogle Scholar

Nicholson ES, Ashworth BT (1977) US Patent, 4013720Google Scholar

Lewis KJ, Mulquiney CE (1977) Aspects of the formation and use of Stenhouse salts and related compounds. Tetrahedron 33:463–475. doi: 10.1016/S0040-4020(77)80002-1 CrossRefGoogle Scholar

Stenhouse J (1850) Ueber die oele, die bei der einwirkung der schwefelsäure auf verschiedene vegetabilien entstehen. J Liebigs Ann Chem 74:278–297. doi: 10.1002/jlac.18500740304 CrossRefGoogle Scholar

McGowan JC (1949) The preparation of bases from the coloured compounds formed by condensation of furfuraldehyde with aromatic amines. J Chem Soc 165:777–779. doi: 10.1039/JR9490000777 CrossRefGoogle Scholar

Stenhouse J (1870) Ueber Furfuranilin und Furfurtoluidin. Justus Liebigs Annalen der Chemie 156:197–205. doi: 10.1002/jlac.18701560212 CrossRefGoogle Scholar

Dieckmann D, Beck B (1905) Ueber Farbstoffe aus Furfurol. Berichte der deutschen chemischen Gesellschaft 38:4122–4125. doi: 10.1002/cber.19050380489 CrossRefGoogle Scholar

Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23:3–25. doi: 10.1016/S0169-409X(00)00129-0

Keller TH, Pichota H, Yin Z (2006) A practical view of ‘druggability’. Curr Opin Chem Biol 10:357–361. doi: 10.1016/j.cbpa.2006.06.014 PubMedCrossRefGoogle Scholar

Minocha A, Long BH (1984) Inhibition of the DNA catenation activity of type II topoisomerase by VP16-213 and VM26. Biochem Biophys Res Commun 122:165–170. doi: 10.1016/0006-291X(84)90454-6 PubMedCrossRefGoogle Scholar

Tsuruo T, Matsuzaki T, Matsushita M, Saito H, Yokokura T (1988) Antitumor effect of CPT-11, a new derivative of camptothecin, against pleiotropic drug-resistant tumors in vitro and in vivo. Cancer Chemother Pharmacol 21:71–74. doi: 10.1007/BF00262744 PubMedCrossRefGoogle Scholar

Drees M, Dengler WA, Roth T, Labonte H, Mayo J, Malspeis L, Grever M, Sausville EA, Fiebig HH (1997) Flavopiridol (L86–8275): selective antitumor activity in vitro and activity in vivo for prostate carcinoma cells. Clin Cancer Res 3:273–279PubMedGoogle Scholar

Raje N, Hideshima T, Mukherjee S, Raab M, Vallet S, Chetri S, Cirstea D, Pozzi S, Mitsiades C, Rooney M, Kiziltepe T, Podar K, Okawa Y, Ikeda H, Carrasco R, Richardson PG, Chauhan D, Munshi NC, Sharma S, Parikh H, Chabner B, Scadden D, Anderson KC (2009) Preclinical activity of P276–00, a novel small-molecule cyclin-dependent kinase inhibitor in the therapy of multiple myeloma. Leukemia 23:961–970. doi: 10.1038/leu.2008.378 PubMedCrossRefGoogle Scholar

Heath EI, Bible K, Martell RE, Adelman DC, Lorusso PM (2008) A phase 1 study of SNS-032 (formerly BMS-387032), a potent inhibitor of cyclin-dependent kinases 2, 7 and 9 administered as a single oral dose and weekly infusion in patients with metastatic refractory solid tumors. Invest New Drugs 26:59–65. doi: 10.1007/s10637-007-9090-3 PubMedCrossRefGoogle Scholar

Mgbonyebi OP, Russo J, Russo IH (1998) Roscovitine inhibits the proliferative activity of immortal and neoplastic human breast epithelial cells. Anticancer Res 18:751–755PubMedGoogle Scholar

Ohno K, Sakai T, Fukushima M, Narumiya S, Fujiwara M (1988) Site and mechanism of growth inhibition by prostaglandins. IV. Effect of cyclopentenone prostaglandins on cell cycle progression of G1-enriched HeLa S3 cells. J Pharmacol Exp Ther 245:294–298PubMedGoogle Scholar

Gorospe M, Liu Y, Xu Q, Chrest FJ, Holbrook NJ (1996) Inhibition of G1 cyclin-dependent kinase activity during growth arrest of human breast carcinoma cells by prostaglandin A2. Mol Cell Biol 16:762–770PubMedPubMedCentralGoogle Scholar