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1
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0026747866
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(a) Kato, K.; Cox, A. D.; Hisaka, M. M.; Graham, S. M.; Buss, J. E. Proc. Natl. Acad. Sci. U.SA. 1992, 89, 6403-6407.
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Kato, K.1
Cox, A.D.2
Hisaka, M.M.3
Graham, S.M.4
Buss, J.E.5
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2
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0032704708
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(b) Rowinsky, E. K.; Windle, J. L.; Von Hoff, D. D. J. Clin. Oncol. 1999, 17, 3631-3652.
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Rowinsky, E.K.1
Windle, J.L.2
Von Hoff, D.D.3
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6
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0042878016
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Boston, MA, American Chemical Society: Washington, DC, 1998; MEDI 309
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(a) Williams, T. M.; Dinsmore. C. J.; Bergman, J. M.; Hutchinson, J. H.; MacTough, S. C.; Stump, C. S.; Wei, D. D.; Zartman, C. B.; Bogusky, M. J.; Chen, I.-W.; Culberson, J. C.; Koblan, K. S.; Kohl, N. E.; Lobell, R. B.; Motzel, S. L.; Salata, J. J.; Gibbs, J. B.; Graham, S. L.; Hartman, G. D.; Oliff, A. I.; Huff, J. R. Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, MA, 1998, American Chemical Society: Washington, DC, 1998; MEDI 309.
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(1998)
Abstracts of Papers, 216th National Meeting of the American Chemical Society
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Williams, T.M.1
Dinsmore, C.J.2
Bergman, J.M.3
Hutchinson, J.H.4
MacTough, S.C.5
Stump, C.S.6
Wei, D.D.7
Zartman, C.B.8
Bogusky, M.J.9
Chen, I.-W.10
Culberson, J.C.11
Koblan, K.S.12
Kohl, N.E.13
Lobell, R.B.14
Motzel, S.L.15
Salata, J.J.16
Gibbs, J.B.17
Graham, S.L.18
Hartman, G.D.19
Oliff, A.I.20
Huff, J.R.21
more..
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7
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0042878693
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Manuscript in preparation
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(b) Manuscript in preparation.
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8
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0041375685
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In liver microsome incubation studies. 1 suffers N-dealkylations of the imidazole and piperazinone rings (unpublished results, ref 3b)
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In liver microsome incubation studies. 1 suffers N-dealkylations of the imidazole and piperazinone rings (unpublished results, ref 3b).
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9
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0015697984
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(a) H2 antagonists: Durant, G. J.; Loynes, J. M.; Wright, S. H. B. J. Med. Chem. 1973, 16, 1272-1276.
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J. Med. Chem.
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Durant, G.J.1
Loynes, J.M.2
Wright, S.H.B.3
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10
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0023277530
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(b) Cardiotonics: Davey, D.; Erhardt, P. W.; Lumma, W. C., Jr.; Wiggins, J.; Sullivan, M.; Pang, D.; Cantor, E. J. Med. Chem. 1987, 30, 1337-1342.
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J. Med. Chem.
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Davey, D.1
Erhardt, P.W.2
Lumma W.C., Jr.3
Wiggins, J.4
Sullivan, M.5
Pang, D.6
Cantor, E.7
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11
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0025970208
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(c) Aromatase inhibitors: Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E.; Bhatnager, A. J. Med. Chem. 1991, 34, 725-736.
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(1991)
J. Med. Chem.
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, pp. 725-736
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Browne, L.J.1
Gude, C.2
Rodriguez, H.3
Steele, R.E.4
Bhatnager, A.5
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12
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0027971764
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(d) A-II antagonists: Huang, H.-C.; Chamberlain, T. S.; Olins, G. M.; Corpus, V. M.; Chen, S. T.; McMahon, E. G.; Palomo, M. A.; Blaine, E. H.; Manning, R. E. Bioorg. Med. Chem. Lett. 1994, 4, 2591-2596.
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(1994)
Bioorg. Med. Chem. Lett.
, vol.4
, pp. 2591-2596
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Huang, H.-C.1
Chamberlain, T.S.2
Olins, G.M.3
Corpus, V.M.4
Chen, S.T.5
McMahon, E.G.6
Palomo, M.A.7
Blaine, E.H.8
Manning, R.E.9
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13
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0028846231
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(e) Glycosidase inhibitors: Frankowski, A.; Deredas, D.; Nouen, D. L.; Tschamber, T.; Streith, J. Helv. Chim. Acta 1995, 78, 1837 -1842.
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(1995)
Helv. Chim. Acta
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, pp. 1837-1842
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Frankowski, A.1
Deredas, D.2
Nouen, D.L.3
Tschamber, T.4
Streith, J.5
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14
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0029899763
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(f) 5-HT3 antagonists: Ohta, M.; Suzuki, T.; Koide, T.; Matsuhisa, A.; Furuya, T.; Miyata, K.; Yanagisawa, I. Chem. Pharm. Bull. 1996, 44, 991-999.
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(1996)
Chem. Pharm. Bull.
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Ohta, M.1
Suzuki, T.2
Koide, T.3
Matsuhisa, A.4
Furuya, T.5
Miyata, K.6
Yanagisawa, I.7
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16
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0042878691
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For the related Pictet-Spengler cyclization of histamine derivatives with aldehydes, see: (a) Heyl, D.; Luz, E.; Harris, S. S.; Folkers, K. J. Am. Chem. Soc. 1948, 70, 3669.
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(1948)
J. Am. Chem. Soc.
, vol.70
, pp. 3669
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Heyl, D.1
Luz, E.2
Harris, S.S.3
Folkers, K.4
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17
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0008308884
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(b) Jouanisson, A.; Chavignon, O.; Couquelet, J.; Teulade, J.-C.; Chabard, J.-L.; Dauphin, G. Heterocycles 1995, 41, 21-28.
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(1995)
Heterocycles
, vol.41
, pp. 21-28
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Jouanisson, A.1
Chavignon, O.2
Couquelet, J.3
Teulade, J.-C.4
Chabard, J.-L.5
Dauphin, G.6
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19
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85088005527
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3 (1.5 equiv) in DMF at room temperature for 4 h (62% for 8b)
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3 (1.5 equiv) in DMF at room temperature for 4 h (62% for 8b).
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20
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12644312578
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Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
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(1978)
J. Org. Chem.
, vol.43
, pp. 2480
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Mancuso, A.J.1
Huang, S.-L.2
Swern, D.3
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21
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0032497606
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Weissman, S. A.; Lewis, S.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 7459-7462.
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(1998)
J. Tetrahedron Lett.
, vol.39
, pp. 7459-7462
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Weissman, S.A.1
Lewis, S.2
Askin, D.3
Volante, R.P.4
Reider, P.5
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22
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0041876457
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note
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4 (1.00 g, 8.3 mmol). The reaction was heated to reflux for 1.5 h, cooled to room temperature, diluted with dichloromethane (300 mL), filtered, and concentrated in vacuo. Purification by flash chromatography (6 × 15 cm silica gel, 40 → 80% acetone/dichloromethane) provided 12 (276 mg, 19%) and trans-2 (455 mg, 31%), both as pale yellow foams.
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23
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0042878690
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note
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+) 446.1742, found 446.1732.
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25
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0028211246
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For assay conditions, see: Graham, S. L.; deSolms, S. J.; Kohl, N. E.; Mosser, S. D.; Oliff, A. I.; Pompliano, D. L.; Rands, E.; Breslin, M. J.; Deanna, A. A.; Garsky, V. M.; Scholz, T. H.; Gibbs, J. B.; Smith, R. L. J. Med. Chem. 1994, 37, 725-737.
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(1994)
J. Med. Chem.
, vol.37
, pp. 725-737
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Graham, S.L.1
DeSolms, S.J.2
Kohl, N.E.3
Mosser, S.D.4
Oliff, A.I.5
Pompliano, D.L.6
Rands, E.7
Breslin, M.J.8
Deanna, A.A.9
Garsky, V.M.10
Scholz, T.H.11
Gibbs, J.B.12
Smith, R.L.13
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26
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0041875822
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The FTase inhibitory activity and dog pharmacokinetic (PK) properties of 1 and the corresponding 2-methylimidazole analogue of 1 are very similar, suggesting that the methyl groups in trans-13 and cis-13 contribute little to their inhibitory and PK activities (Merck Research Laboratories, unpublished results)
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The FTase inhibitory activity and dog pharmacokinetic (PK) properties of 1 and the corresponding 2-methylimidazole analogue of 1 are very similar, suggesting that the methyl groups in trans-13 and cis-13 contribute little to their inhibitory and PK activities (Merck Research Laboratories, unpublished results).
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27
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0042376922
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note
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(a) Molecular modeling results, with relative energies in kcal/mol shown in parentheses: trans-13 diequatorial half-chair (0.00); trans-13 diaxial half-chair (1.56); cis-13 equatorial-)ArCN) - axial-(piperazinone) half-chair (0.18); cis-13 axial-(ArCN) - equatorial-(piperazinone) half-chair (0.59); cis-13 diaxial boat (5.46). Conformations were generated using the metric matrix distance geometry algorithm JG (S. Kearsley, Merck Research Laboratories, unpublished). The structures were subjected to energy-minimization within Macromodel (ref 15b) using the MMFF force field.
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28
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84986437005
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(b) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
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(1990)
J. Comput. Chem.
, vol.11
, pp. 440-467
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Mohamadi, F.1
Richards, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Caufield, C.5
Chang, G.6
Hendrickson, T.7
Still, W.C.8
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29
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0031048025
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For the protocol for PK analysis, see: Olah, T. V.; McLoughlin, D. A.; Gilbert, J. D. Rapid Commun. Mass Spectrom. 1997, 11, 17-23.
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(1997)
Rapid Commun. Mass Spectrom.
, vol.11
, pp. 17-23
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Olah, T.V.1
McLoughlin, D.A.2
Gilbert, J.D.3
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30
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85088005915
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1/2 10.3 h) relative to 1 (2 mpk: CL = 10.6 mL/min/kg)
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1/2 10.3 h) relative to 1 (2 mpk: CL = 10.6 mL/min/kg).
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