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Chemical Compound Review

COMPOUND 9     5-[2-fluoro-5-[(E)-3-(3- hydroxy-2...

Synonyms: CHEMBL117869, SureCN5620738, DB02014, AC1L9LH8, 1q1m, ...
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Disease relevance of COMPOUND 9


Psychiatry related information on COMPOUND 9

  • Compound 9 (1mg/kg, i.p.) was fully efficacious in reverting scopolamine-induced amnesia in mice [6].

High impact information on COMPOUND 9

  • These compounds, and in particular compound 9, also showed excellent inhibitory activity against both HIV-112 and HIV-AB1 primary isolates in lymphocytes and against HIV WT in macrophages [7].
  • The results suggest therefore that compound 9 is a potent new tool for the accurate mapping of the human V(1a) receptor antagonist binding site [8].
  • The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2) [9].
  • Compound 9 increases c-fos mRNA level as does PGE(2) and antagonizes TPA-induced terminal differentiation [9].
  • The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29) [10].

Chemical compound and disease context of COMPOUND 9

  • Compound 14 showed inhibition of HIV-1 with EC(50) > 1.6 mug mL(-1), meanwhile compound 9 exhibited activity against leukaemia (MT4) with CC(50) = 24 mumol L(-1) [11].

Biological context of COMPOUND 9


Anatomical context of COMPOUND 9

  • Compound 9 with the 6-purine-substituted pyrrolo moiety had a more pronounced selective cytostatic activity against human (Molt4/C8 and CEM/0) cell lines than murine (L1210/0 and FM3A/0) and human (MiaPaCa2, MCF7, HeLa, and Hep2) tumor cell lines and normal fibroblasts (Hef522) [17].
  • The influence of the compound 9 on the central nervous system (CNS) of mice in some behavioural test was examined [18].
  • Two new conformationally constrained benzimidazole derivatives were prepared and their binding affinity was tested on rat brain membranes; compound 9, designed to reproduce the conformation of a known potent H(3) antagonist, showed higher potency than compound 8, as expected from the binding scheme hypothesized [19].
  • The title compound 9, which is a prodrug, and its active metabolite 7 were labelled with 131I (7*/9*) to investigate their pharmacokinetic behaviour, including the distribution between stomach, gut, muscle, blood, lung, liver, kidney, adrenal gland, heart, and spleen [20].
  • Compound 9 (2-[4'-(iso-propylphenyl)-amino]-5,6-dimethyl-1,4-benzoquinone) was identified as the most potent aminoquinone derivative, suppressing 5-lipoxygenase in intact human polymorphonuclear leukocytes as well as in crude enzyme preparations in the low micromolar range (IC(50) = 6 microM) [21].

Associations of COMPOUND 9 with other chemical compounds

  • At pH 2.2 and 3.4, the two hydrolytic pathways coexist since, beside compounds 2 and 3, the hydrochloride of compound 9 [Cl(CH2)2NH(CH2)2NH(CH2)3OP(O)(OH)2] is formed, resulting from the acid-catalyzed breakdown of the P-N bond in the nine-membered ring compound 13 [22].
  • To permit detailed biochemical studies regarding interaction of the indazole class of serotonin (5HT) antagonists with 5HT3 receptors in multiple tissues, we synthesized 1-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazole- 3-carboxamide (LY278584, compound 9) in high specific activity, tritium-labeled form [23].
  • Compound 9, a reversed amidine, exhibited the highest activity against L. infantum, with a 50% inhibitory concentration (IC(50)) of 0.0042muM compared with 14.2muM for pentamidine [24].
  • In addition, compound 9 exhibited more potent MDR modulating activity than verapamil, a representative modulator of MDR mediated by P-gp [25].
  • A significant decrease in MCF-7 cell proliferation was observed using 1 microM and 10 microM compound (11) and 10 microM of compound (9) [26].

Gene context of COMPOUND 9

  • The activity of cyclooxygenase (COX)-1 was inhibited slightly by compound 9, but that of COX-2 was not inhibited [27].
  • A treatment with 100 microM of compound 9 for 24 h resulted in a 50% decrease of COX-2 promoter activity without marked cytotoxicity [28].
  • Moreover, to predict how the thieno[3,2-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure [29].
  • Seeking to improve the properties of 3 led to the synthesis of compound 9, a highly selective mGlu5 receptor antagonist that is 5-fold more potent than 3 in the rat fear-potentiated startle model of anxiety [30].
  • Compound 9 was a potent competitive inhibitor of MTA phosphorylase with a Ki value of 3.3 microM and was also a substrate, with activity approximately 53% that of MTA [31].

Analytical, diagnostic and therapeutic context of COMPOUND 9


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  7. Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide. Ragno, R., Coluccia, A., La Regina, G., De Martino, G., Piscitelli, F., Lavecchia, A., Novellino, E., Bergamini, A., Ciaprini, C., Sinistro, A., Maga, G., Crespan, E., Artico, M., Silvestri, R. J. Med. Chem. (2006) [Pubmed]
  8. Design of benzophenone-containing photoactivatable linear vasopressin antagonists: pharmacological and photoreactive properties. Ponthieux, S., Cabot, J., Mouillac, B., Seyer, R., Barberis, C., Carnazzi, E. J. Med. Chem. (2005) [Pubmed]
  9. Enantioselective synthesis and biological activity of (3S,4R)- and (3S,4S)-3-hydroxy-4-hydroxymethyl- 4-butanolides in relation to PGE2. Miranda, P.O., Estévez, F., Quintana, J., García, C.I., Brouard, I., Padrón, J.I., Pivel, J.P., Bermejo, J. J. Med. Chem. (2004) [Pubmed]
  10. New analogues of amonafide and elinafide, containing aromatic heterocycles: synthesis, antitumor activity, molecular modeling, and DNA binding properties. Braña, M.F., Cacho, M., García, M.A., de Pascual-Teresa, B., Ramos, A., Domínguez, M.T., Pozuelo, J.M., Abradelo, C., Rey-Stolle, M.F., Yuste, M., Báñez-Coronel, M., Lacal, J.C. J. Med. Chem. (2004) [Pubmed]
  11. Amino acid derivatives. Part I. Synthesis, antiviral and antitumor evaluation of new alpha-amino acid esters bearing coumarin side chain. Al-Masoudi, N.A., Al-Masoudi, I.A., Ali, I.A., Al-Soud, Y.A., Saeed, B., LA Colla, P. Acta pharmaceutica (Zagreb, Croatia) (2006) [Pubmed]
  12. Derivatives of 2-methylenepropane-1,3-diol as new antagonists of platelet activating factor. Grue-Sørensen, G., Nielsen, I.M., Nielsen, C.K. J. Med. Chem. (1988) [Pubmed]
  13. Total synthesis of woodrosin I--part 2: final stages involving RCM and an orthoester rearrangement. Fürstner, A., Jeanjean, F., Razon, P., Wirtz, C., Mynott, R. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  14. Synthesis and antitumor cytotoxicity evaluation of pyrido[4,3,2-de]quinolines and isoquinolino[6,5,4,3-cde]quinolines. Ding, Q., Jia, G., Lown, J.W. Anticancer Drug Des. (2000) [Pubmed]
  15. Synthesis and anticancer activities of 5,6,7-trimethylbaicalein derivatives. Liao, H.L., Hu, M.K. Chem. Pharm. Bull. (2004) [Pubmed]
  16. Novel diphenylalkyl piperazine derivatives with dual calcium antagonistic and antioxidative activities. Kimura, M., Masuda, T., Yamada, K., Kubota, N., Kawakatsu, N., Mitani, M., Kishii, K., Inazu, M., Namiki, T. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  17. Novel pyrimidine and purine derivatives of L-ascorbic acid: synthesis and biological evaluation. Raić-Malić, S., Hergold-Brundić, A., Nagl, A., Grdisa, M., Pavelić, K., De Clercq, E., Mintas, M. J. Med. Chem. (1999) [Pubmed]
  18. Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Modzelewska-Banachiewicz, B., Banachiewicz, J., Chodkowska, A., Jagiełło-Wójtowicz, E., Mazur, L. European journal of medicinal chemistry. (2004) [Pubmed]
  19. Validation of a histamine H3 receptor model through structure-activity relationships for classical H3 antagonists. Lorenzi, S., Mor, M., Bordi, F., Rivara, S., Rivara, M., Morini, G., Bertoni, S., Ballabeni, V., Barocelli, E., Plazzi, P.V. Bioorg. Med. Chem. (2005) [Pubmed]
  20. Distribution behaviour of 131-iodine labelled trans-N,N'-bis-(ethoxy-carbonyl)-N-[4-(3-iodo-4-methoxyphenyl)butyl]-N' -5- phenylpentyl)-1,4-cyclohexanedimethanamine. Rehse, K., Wolf, S., Buck, W., Wenzel, M. Arch. Pharm. (Weinheim) (1995) [Pubmed]
  21. Inhibition of human 5-lipoxygenase and anti-neoplastic effects by 2-amino-1,4-benzoquinones. Poeckel, D., Niedermeyer, T.H., Pham, H.T., Mikolasch, A., Mundt, S., Lindequist, U., Lalk, M., Werz, O. Medicinal chemistry (Sh???ariqah, United Arab Emirates) (2006) [Pubmed]
  22. Chemical and biological evaluation of hydrolysis products of cyclophosphamide. Gilard, V., Martino, R., Malet-Martino, M.C., Kutscher, B., Müller, A., Niemeyer, U., Pohl, J., Polymeropoulos, E.E. J. Med. Chem. (1994) [Pubmed]
  23. Synthesis and biochemical evaluation of tritium-labeled 1-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazole-3-carboxa mide, a useful radioligand for 5HT3 receptors. Robertson, D.W., Bloomquist, W., Cohen, M.L., Reid, L.R., Schenck, K., Wong, D.T. J. Med. Chem. (1990) [Pubmed]
  24. In vitro activity of dicationic compounds against a North American foxhound isolate of Leishmania infantum. Rosypal, A.C., Hall, J.E., Bakunova, S., Patrick, D.A., Bakunov, S., Stephens, C.E., Kumar, A., Boykin, D.W., Tidwell, R.R. Vet. Parasitol. (2007) [Pubmed]
  25. Facilely accessible multidrug resistance modulator derived from sucrose. Murakami, N., Tamura, S., Iwata, E., Aoki, S., Akiyama, S., Kobayashi, M. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  26. Anti-proliferative effects of novel glyco-lipid-arsenicals (III) on MCF-7 human breast cancer cells. Wimmer, N., Robinson, J.A., Gopisetty-Venkata, N., Roberts-Thomson, S.J., Monteith, G.R., Toth, I. Medicinal chemistry (Sh⁻ariqah, United Arab Emirates) (2006) [Pubmed]
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  28. Syntheses of ferulic acid derivatives and their suppressive effects on cyclooxygenase-2 promoter activity. Hosoda, A., Ozaki, Y., Kashiwada, A., Mutoh, M., Wakabayashi, K., Mizuno, K., Nomura, E., Taniguchi, H. Bioorg. Med. Chem. (2002) [Pubmed]
  29. Preparation of thieno[3,2-h]cinnolinones as matrix metalloproteinase inhibitors. Pinna, G.A., Curzu, M.M., Murineddu, G., Chelucci, G., Cignarella, G., Menta, E., Krell, H.W., Rastelli, G., Ferrari, A.M. Arch. Pharm. (Weinheim) (2000) [Pubmed]
  30. 3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: a potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity. Cosford, N.D., Tehrani, L., Roppe, J., Schweiger, E., Smith, N.D., Anderson, J., Bristow, L., Brodkin, J., Jiang, X., McDonald, I., Rao, S., Washburn, M., Varney, M.A. J. Med. Chem. (2003) [Pubmed]
  31. Synthesis and antiproliferative effects of novel 5'-fluorinated analogues of 5'-deoxy-5'-(methylthio)adenosine. Sufrin, J.R., Spiess, A.J., Kramer, D.L., Libby, P.R., Porter, C.W. J. Med. Chem. (1989) [Pubmed]
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