Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives

Chan, Wai‐Lun; Dd, Ho; Lau, CP; Wat, K. H.; Cheng, K. F.; Wong, TT; Chan, T. Y.

doi:10.1016/0223-5234(91)90099-9

Cited by 22 publications

(1 citation statement)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5-Methoxy-1-( p -tolylsulfonyl)indole-3-carboxaldehyde, 3c. This material was obtained in 90% yield as an off-white powder: mp 124−126 °C, lit . mp 128−129 °C; 1 H NMR δ 10.06 (s, 1H, CHO), 8.17 (s, 1H, ArH), 7.82 (d, 3H, ArH, J = 8.8 Hz), 7.70 (d, 1H, ArH, J = 2.3 Hz), 7.28 (d, 2H, ArH, J = 8.8 Hz), 7.00 (dd, 1H, ArH, J = 9.0 and 2.6 Hz), 3.85 (s, 3H, ArOCH 3 ), 2.37 (s, 3H, ArCH 3 ); CIMS 330 (MH + ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Serotonin Receptor Affinities of a Series of trans-2-(Indol-3-yl)cyclopropylamine Derivatives

et al. 1998

View full text Add to dashboard Cite

A series of four racemic ring-substituted trans-2-(indol-3-yl)cyclopropylamine derivatives was synthesized and tested for affinity at the 5-HT1A receptor, by competition with [3H]-8-OH-DPAT in rat hippocampal homogenates, and for affinity at the agonist-labeled cloned human 5-HT2A, 5-HT2B, and 5-HT2C receptor subtypes. None of the compounds had high affinity for the 5-HT1A receptor, with the 5-methoxy substitution being most potent (40 nM). At the 5-HT2A and 5-HT2B receptor isoforms, most of the compounds lacked high affinity. At the 5-HT2C receptor, however, affinities were considerably higher. The 5-fluoro-substituted compound was most potent, with a Ki at the 5-HT2C receptor of 1.9 nM. In addition, the 1R,2S-(-) and 1S,2R-(+) enantiomers of the unsubstituted compound were also evaluated at the 5-HT2 isoforms. While the 1R,2S enantiomer had higher affinity at the 5-HT2A and 5-HT2B sites, the 1S,2R isomer had highest affinity at the 5-HT2C receptor. This reversal of stereoselectivity may offer leads to the development of a selective 5-HT2C receptor agonist. The cyclopropylamine moiety therefore appears to be a good strategy for rigidification of the ethylamine side chain only for tryptamines that bind to the 5-HT2C receptor isoform.

show abstract

Section: Methodsmentioning

confidence: 99%