Relationship between electronic structure and cytotoxic activity of dopamine and 3-benzazepine derivatives

In Vivo

Volumn 18, Issue 4, 2004, Pages 443-448

  Kurihara, Teruo ^a   Yamada, Tomoya ^a   Yamamoto, Ayoko ^a   Kawase, Masami ^a   Motohashi, Noboru ^b   Sakagami, Hiroshi ^c   Molnár, Joseph ^d  

^a JOSAI UNIVERSITY   (Japan)

^b MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^c MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^d UNIVERSITY OF SZEGED   (Hungary)

Author keywords

3 benzazepines; Dipole moment ( ); Dopamines

Indexed keywords

2,3,4,5 TETRAHYDRO 3 BENZAZEPINE DERIVATIVE; 2,3,4,5 TETRAHYDRO 3 BENZAZEPINONE DERIVATIVE; 3 BENZAZEPINE DERIVATIVE; DOPAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIPOLE; DRUG CYTOTOXICITY; DRUG STRUCTURE; GAS; PARTITION COEFFICIENT; PHASE TRANSITION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 4444254103     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Winstock J, Hieble JP and Wilson JW: The chemistry and pharmacology of 3-benzazepines. Drugs Future 10: 645-96, 1985.
2. Berek L, Petri IB, Varga E, Molnár J, Kawase M, Saito S and Motohashi N: Immunomodulating effect of 2,3,4,5-tetrahydro-1H-3-benzazepines (a new class of non-nucleoside inhibitors of reverse transcriptase). Int J Antimicrob Agents 14: 221-224, 2000.
3. Motohashi N, Kawase M, Saito S, Miskolci C, Berek L and Molnár J: Plasmid elimination and immunomodulation by 3-benzazepines in vitro. Anticancer Res 19: 5075-5078, 1999.
4. Kawase M, Saito S and Motohashi N: Chemistry and biological activity of new 3-benzazepines. Int J Antimicrob Agents 14: 193-201, 2000.
5. Daly RN, Sulpizio AC, Levitt B, DeMarinis RM, Regan JW, Ruffolo RR and Hieble JP: Evidence for heterogeneity between pre- and postjunctional alpha-2 adrenoceptors using 9-substituted 3-benzazepines. J Pharmacol Exp Ther 247: 122-128, 1988.
6. Wunsch B, Nerdinger S, Bauschke G and Hofner G: Noncompetitive NMDA antagonists: a novel synthesis of 1-phenyltetrahydro-3-benzazepines. Arch Pharm (Weinheim) 330: 211-4, 1997.
7. Gombar CT, Demarinis RM, Wise M and Mico BA: Pharmacokinetics of a series of 6-chloro-2,3,4,5-tetrahydro-3-substituted-1H-3-benzazepines in rats. Determination of quantitative structure-pharmacokinetic relationships. Drug Metab Dispos 16: 367-372, 1988.
8. Weinstock J, Oh HJ, DeBrosse CW, Eggleston DS, Wise M, Flaim KE, Gessner GW, Sawyer JL and Kaiser C: Synthesis, conformation, and dopaminergic activity of 5, 6-ethano-bridged derivatives of selective dopaminergic 3-benzazepines. J Med Chem 30: 1303-1308, 1987.
9. Ladd DL, Weinstock J, Wise M, Gessner GW, Sawyer JL and Flaim KE: Synthesis and dopaminergic binding of 2-aryldopamine analogues: phenethylamines, 3-benzazepines, and 9-(aminomethyl)fluorenes. J Med Chem 29: 1904-1912, 1986.
10. Ross ST, Franz RG, Wilson JW, Brenner M, DeMarinis RM, Hieble JP and Sarau HM: Dopamine receptor agonists: 3-allyl-6-chloro-2,3,4,5- tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol and a series of related 3-benzazepines. J Med Chem 29: 733-740, 1986.
11. Kawase M, Motohashi N, Niwa M and Nozaki M: Use of the triflamide group for Friedel-Crafts acylation of N-(β-phenethyl amino acids to 3-benzazepine derivatives. Heterocycles 45: 1121-9,1997.
12. Kawase M, Niwa M, Nozaki M and Motohashi N: Synthesis of 2-trifluoromethyl-2,3,4,5-tetrahydro-1H-3-benazepine derivatives. Heterocycles 48: 555-60,1998.
13. PM3 semi-emprical MO calculations were performed by MOPAC version 6 on an IBM aptiva E47 personal computer.
14. Ohkura K and Hori H: Analysis of structure-permeability correlation of nitrophenol analoges in newborn rat abdominal skin using semiempirical molecular orbital calculation. Bioorg Med Chem 7: 309-314, 1998.
15. Kawase M, Motohashi N, Kurihara T, Inagaki M, Satoh K and Sakagami H: Relationship between radical intensity and cytotoxic activity of dopamine-related compounds. Anticancer Res 18: 1069-1074, 1998.