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Volumn 17, Issue 11, 2007, Pages 3099-3104

Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors

Author keywords

Homotryptamine; Serotonin transporter; SSRI

Indexed keywords

AMINE; CYCLOHEXENYLAMINE DERIVATIVE; INDOLE; INDOLE TETRAHYDROPYRIDINE DERIVATIVE; N METHYL TETRAHYDROPYRID 4 YL INDOLE DERIVATIVE; N,N DIMETHYLAMINE; N,N DIMETHYLAMINO CYCLOHEXEN 4 YL INDOLE DERIVATIVE; NITRILE; SEROTONIN TRANSPORTER; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

EID: 34247877756     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.03.040     Document Type: Article
Times cited : (41)

References (30)
  • 14
    • 34247848670 scopus 로고    scopus 로고
    • note
    • 6): δ 8.26 (s, 1H), 7.56 (d, J = 8.4, 1H), 7.50 (s, 1H), 7.38 (m, 1H), 6.22 (m, 1H), 2.60 (m, 1H), 2.27 (s, 6H), 2.46 (m, 3H), 2.21 (m, 1H), 2.05 (m, 1H), and 1.55 (m, 1H).
  • 16
    • 34247852591 scopus 로고    scopus 로고
    • note
    • 2/12% ethanol with 0.1% diethylamine, 50 mL/min @ 150 bar, peak 2 corresponds to R-6a.
  • 17
    • 34247845327 scopus 로고    scopus 로고
    • note
    • Full crystallographic data have been deposited to the Cambridge Crystallographic Data Center (CCDC reference number 615920). Copies of the data can be obtained free of charge via the internet at http://www.ccdc.cam.ac.uk.
  • 18
    • 34247872196 scopus 로고    scopus 로고
    • note
    • 50 > 500. n = 5 for compound 6a.
  • 19
    • 34247870611 scopus 로고    scopus 로고
    • note
    • Analytical data for (R)-3-(4-(dimethylamino)cyclohex-1-enyl)-1H-indole-5-carbonitrile, compound R-6a: HPLC purity: >98%; >99%ee; Optical rotation: +51.9 (methanol, c = 3.0 mg/mL).
  • 20
    • 34247890922 scopus 로고    scopus 로고
    • note
    • 50 data was determined from a 20-point curve. Non-specific binding was defined using 10 μM Fluoxetine for SERT, 100 μM Desipramine for NET, and 10 μM GBR-12935 for DAT.
  • 22
    • 34247867292 scopus 로고    scopus 로고
    • g The RMS fitting of (S)-citalopram to sertraline included a fourth pair of points corresponding to the centroids of the fluorophenyl ring in (S)-citalopram, and the non-chlorinated phenyl ring in sertraline. The superposition shown in Figure 7 was generated by RMS fitting the low-energy conformers of R-6a, S-6a, 3, and 4 to the sertraline reference conformer as described above for R-6a and S-6a. In both figures, all other compounds were fit to sertraline, even though it is not shown explicitly in Figure 7.
  • 27
    • 34247886809 scopus 로고    scopus 로고
    • See: Jaguar 6.5 Operating Manual; Schrodinger, LLC: New York, NY, 2005, and references therein.
  • 29
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    • A Stereoselective Pharmacophoric Model of the Serotonin Re-Uptake Site
    • van de Waterbeemd H., Testa B., and Folkers G. (Eds), Verlag Helvetica Chimica Acta, Basel, Switzerland
    • Gundertofte K., Bøgesø K.P., and Liljefors T. A Stereoselective Pharmacophoric Model of the Serotonin Re-Uptake Site. In: van de Waterbeemd H., Testa B., and Folkers G. (Eds). Computer-Assisted Lead Finding and Optimization: Current Tools for Medicinal Chemistry (1997), Verlag Helvetica Chimica Acta, Basel, Switzerland 443-459
    • (1997) Computer-Assisted Lead Finding and Optimization: Current Tools for Medicinal Chemistry , pp. 443-459
    • Gundertofte, K.1    Bøgesø, K.P.2    Liljefors, T.3
  • 30
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    • In-house results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.