• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors.

作者信息

Toyooka Naoki, Kobayashi Soushi, Zhou Dejun, Tsuneki Hiroshi, Wada Tsutomu, Sakai Hideki, Nemoto Hideo, Sasaoka Toshiyasu, Garraffo H Martin, Spande Thomas F, Daly John W

机构信息

Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan.

出版信息

Bioorg Med Chem Lett. 2007 Nov 1;17(21):5872-5. doi: 10.1016/j.bmcl.2007.08.045. Epub 2007 Aug 26.

DOI:10.1016/j.bmcl.2007.08.045
PMID:17827002
Abstract

We previously reported that the synthetic quinolizidine 1-epi-207I is a relatively selective blocker of alpha7 nicotinic acetylcholine receptors. We now synthesized the analogous poison frog alkaloids 233A, 235U, and 251AA, and investigated the biological activities at two major types of neuronal nicotinic receptors. Electrophysiological study showed that the alkaloid 233A blocked alpha7 and alpha4beta2 currents with similar potencies. Alkaloids 235U and 251AA also showed similar potencies for blockade of alpha7 and alpha4beta2 currents. Thus, based on these studies, it would appear that C4 substituents greater in length than the allyl of 1-epi-207I reduce alpha7-potency without affecting alpha4beta2-potency.

摘要

相似文献

1
Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors.
Bioorg Med Chem Lett. 2007 Nov 1;17(21):5872-5. doi: 10.1016/j.bmcl.2007.08.045. Epub 2007 Aug 26.
2
Alkaloids indolizidine 235B', quinolizidine 1-epi-207I, and the tricyclic 205B are potent and selective noncompetitive inhibitors of nicotinic acetylcholine receptors.生物碱中氮茚啶235B'、喹诺里西啶1-表-207I和三环类化合物205B是烟碱型乙酰胆碱受体的强效且选择性非竞争性抑制剂。
Mol Pharmacol. 2004 Oct;66(4):1061-9. doi: 10.1124/mol.104.000729. Epub 2004 Jul 16.
3
Marine alkaloids (-)-pictamine and (-)-lepadin B block neuronal nicotinic acetylcholine receptors.海洋生物碱（-）-匹他明和（-）-柄海鞘素B可阻断神经元烟碱型乙酰胆碱受体。
Biol Pharm Bull. 2005 Apr;28(4):611-4. doi: 10.1248/bpb.28.611.
4
Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors.灵活合成 5,8-取代吲哚里西啶类毒蛙生物碱。II：(-)-209B、(-)-231C、(-)-233D、(-)-235B"、(-)-221I 和 193E 的差向异构体的合成及对神经元烟碱型乙酰胆碱受体的药理学作用。
Beilstein J Org Chem. 2007;3:30. doi: 10.1186/1860-5397-3-30. Epub 2007 Sep 28.
5
Erythrina mulungu alkaloids are potent inhibitors of neuronal nicotinic receptor currents in mammalian cells.红雀珊瑚生物碱是哺乳动物细胞中神经元烟碱型受体电流的有效抑制剂。
PLoS One. 2013 Dec 13;8(12):e82726. doi: 10.1371/journal.pone.0082726. eCollection 2013.
6
Synthesis of poison-frog alkaloids 237D, 207A, and two congeners of 235B' for evaluation to inhibitory effect of nicotinic acetylcholine receptors.
Chem Pharm Bull (Tokyo). 2005 May;53(5):555-60. doi: 10.1248/cpb.53.555.
7
Identification and synthesis of novel alkaloids from the root system of Nicotiana tabacum: affinity for neuronal nicotinic acetylcholine receptors.从烟草根系中鉴定和合成新型生物碱：对神经元烟碱型乙酰胆碱受体的亲和力。
Life Sci. 2005 Dec 22;78(5):495-505. doi: 10.1016/j.lfs.2005.09.009. Epub 2005 Sep 28.
8
Lycaconitine revisited: partial synthesis and neuronal nicotinic acetylcholine receptor affinities.
J Nat Prod. 1996 Jul;59(7):707-9. doi: 10.1021/np960352c.
9
Differential blockade of rat alpha3beta4 and alpha7 neuronal nicotinic receptors by omega-conotoxin MVIIC, omega-conotoxin GVIA and diltiazem.ω-芋螺毒素MVIIC、ω-芋螺毒素GVIA和地尔硫䓬对大鼠α3β4和α7神经元烟碱型受体的差异性阻断作用
Br J Pharmacol. 1999 Jul;127(6):1375-87. doi: 10.1038/sj.bjp.0702692.
10
Involvement of alpha7- and alpha4beta2-type postsynaptic nicotinic acetylcholine receptors in nicotine-induced excitation of dopaminergic neurons in the substantia nigra: a patch clamp and single-cell PCR study using acutely dissociated nigral neurons.α7型和α4β2型突触后烟碱型乙酰胆碱受体参与尼古丁诱导的黑质多巴胺能神经元兴奋：一项使用急性分离的黑质神经元进行的膜片钳和单细胞PCR研究
Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):1-7. doi: 10.1016/j.molbrainres.2004.06.040.

引用本文的文献

1
Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent--195A and -211A.全合成十氢喹啉毒蛙生物碱 ent--195A 和 -211A。
Molecules. 2021 Dec 12;26(24):7529. doi: 10.3390/molecules26247529.
2
Simulations of Promising Indolizidine-6-2 Nicotinic Acetylcholine Receptor Complexes.有前景的吲哚里西啶-6-2 烟碱型乙酰胆碱受体复合物的模拟。
Int J Mol Sci. 2021 Jul 25;22(15):7934. doi: 10.3390/ijms22157934.
3
Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor.
金属有机手性骨架：一种从共同前体制备区域和立体发散的三取代吗啉的对映选择性构建的策略。
J Am Chem Soc. 2011 May 18;133(19):7517-27. doi: 10.1021/ja201012p. Epub 2011 Apr 22.
4
Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.毒蛙生物碱251O和反式-223B的高效对映体和非对映体发散合成。
J Org Chem. 2009 Sep 4;74(17):6784-91. doi: 10.1021/jo901100m.
5
Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus).从 Bufonid 蟾蜍（Melanophryniscus）中提取的假定结构生物碱 5,9E-259B 对应的两种非对映吲哚里西啶的简便合成。
Beilstein J Org Chem. 2008 Jan 21;4:6. doi: 10.1186/1860-5397-4-6.