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N-(3-酰氧基-2-苄基丙基)-N'-[4-(甲基磺酰氨基)苄基]硫脲类似物作为香草酸受体拮抗剂的“B区域”构效关系分析：一种具有强效镇痛活性的N-羟基硫脲类似物的发现

Analysis of structure-activity relationships for the 'B-region' of N-(3-acyloxy-2-benzylpropyl)-N(')-[4-(methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: discovery of an N-hydroxythiourea analogue with potent analgesic activity.

作者信息

Lee Jeewoo, Kang Sang-Uk, Choi Hyun-Kyung, Lee Jiyoun, Lim Ju-Ok, Kil Min-Jung, Jin Mi-Kyung, Kim Kang-Pil, Sung Jong-Hyuk, Chung Suk-Jae, Ha Hee-Jin, Kim Young-Ho, Pearce Larry V, Tran Richard, Lundberg Daniel J, Wang Yun, Toth Attila, Blumberg Peter M

机构信息

Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Shinlim-Dong, Kwanak-Ku, Seoul 151-742, South Korea.

出版信息

Bioorg Med Chem Lett. 2004 May 3;14(9):2291-7. doi: 10.1016/j.bmcl.2004.02.002.

DOI:10.1016/j.bmcl.2004.02.002
PMID:15081027
Abstract

The structural modifications on the B-region of the potent and high affinity vanilloid receptor (VR1) lead ligand N-(3-acyloxy-2-benzylpropyl)-N(')-[4-(methylsulfonylamino)benzyl]thiourea were investigated by the replacement of the thiourea with diverse isosteric functional groups. Structure-activity analysis indicated that the A-region in this series was the primary factor in determining the agonistic/antagonistic activities regardless of the B-region. The N(C)-hydroxy thiourea analogues (12, 13) showed excellent analgesic activities in the acetic acid writhing assay compared to the parent thiourea analogues.

摘要

通过用多种等排功能基团取代硫脲，研究了强效高亲和力香草酸受体（VR1）配体N-(3-酰氧基-2-苄基丙基)-N'-[4-(甲基磺酰氨基)苄基]硫脲B区域的结构修饰。构效关系分析表明，无论B区域如何，该系列中的A区域都是决定激动/拮抗活性的主要因素。与母体硫脲类似物相比，N(C)-羟基硫脲类似物（12, 13）在醋酸扭体试验中表现出优异的镇痛活性。

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