(+/-)-Ecgonidine methyl ester | 127379-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+/-)-Ecgonidine methyl ester
• 英文别名: 8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester；anhydroecgonine methyl ester；ecgonidine methylate；8-methyl-nortrop-2-ene-2-carboxylic acid methyl ester；methyl (1RS)-8-methyl-8-azabicyclo-[3.2.1]oct-2-ene-2-carboxylate；Methyl 8-methyl-8-azabicyclo[3.2.1]oct-3-ene-4-carboxylate；methyl 8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 127379-24-2
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MPSNEAHFGOEKBI-UHFFFAOYSA-N

物化性质

• 沸点：
  72-73 °C(Press: 0.45 Torr)
• 密度：
  1.112±0.06 g/cm3(Predicted)
• 碰撞截面：
  141.14 Ų [M+H]+
• 保留指数：
  1337.2

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-Ecgonidine methyl ester 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 碘 、 sodium carbonate 、 magnesium 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 水 为溶剂， -40.0~80.0 ℃ 、275.79 kPa 条件下， 反应 25.0h， 生成 3β-(4'-amino-biphenyl-4-yl)-8-methyl-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester
  参考文献：
  名称：

  Design and Synthesis of a Novel Photoaffinity Ligand for the Dopamine and Serotonin Transporters Based on 2β-Carbomethoxy-3β-biphenyltropane

  摘要：

  Tropane-based photoaffinity ligands covalently bind to discrete points of attachment on the dopamine transporter (DAT). To further explore structure-activity relations, a ligand in which the photoactivated group was extended from the 3-position of the tropane ring was synthesized from cocaine via a Stille or Suzuki coupling strategy. 3-(4'-Azido-3'-iodo-biphenyl-4-yl)-8-methyl-8-aza-bicyclo[3.2.1] octane-2-carboxylic acid methyl ester (11; K-i = 15.1 +/- 2.2 nM) demonstrated high binding affinity for the DAT. Moreover, this compound showed moderate binding affinity for the serotonin transporter (SERT, K-i = 109 +/- 14 nM), suggesting the potential utility of [I-125] 11 in both DAT and SERT protein structure studies.

  DOI：

  10.1021/jm0603973
• 作为产物：
  描述：

  古卡因 在 盐酸 、 三氯氧磷 作用下， 反应 20.33h， 生成 (+/-)-Ecgonidine methyl ester
  参考文献：
  名称：

  Radical cyclization strategies for the formation of ring constrained tricyclic tropane analogues

  摘要：

  A concise and efficient method for the construction of N,C3-constrained tropane derivatives has been developed. The key step of the reaction sequence involves either a 6- or a 7-trig radical cyclization. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01288-0

文献信息

• Skeletal diversity construction via a branching synthetic strategy
  作者：Emma E. Wyatt、Suzanne Fergus、Warren R. J. D. Galloway、Andreas Bender、David J. Fox、Alleyn T. Plowright、Alan S. Jessiman、Martin Welch、David R. Spring

  DOI：10.1039/b607710b

  日期：——

  A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated.

  一种分支合成策略被用来高效生成结构多样的骨架，覆盖了广泛的化学描述空间，并且证明了它们对耐甲氧西林金黄色葡萄球菌（MRSA）的生物活性。
• COMPOUNDS AND METHODS FOR PREVENTING OR TREATING SENSORY HAIR CELL DEATH
  申请人：University of Washington

  公开号：US20160229869A1

  公开（公告）日：2016-08-11

  Disclosed herein are compounds, and pharmaceutical compositions that include such compounds, for preventing or treating hearing loss. The compounds and pharmaceutical compositions described herein prevent or treat hair cell death. In addition, the compounds and pharmaceutical compositions described herein protect against kidney damage in an individual receiving an aminoglycoside antibiotic. Methods of using the compounds, alone or in combination with other therapeutic agents, are also disclosed.

  本文揭示了一些化合物和包含这些化合物的药物组合物，用于预防或治疗听力损失。本文描述的化合物和药物组合物可以预防或治疗毛细胞死亡。此外，本文描述的化合物和药物组合物可以保护接受氨基糖苷类抗生素的个体免受肾脏损伤。还公开了使用这些化合物的方法，单独或与其他治疗剂联合使用。
• Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 Labeled 2β-Carbomethoxy-3β-(3‘-((<i>Z</i>)-2-haloethenyl)phenyl)nortropanes:  Candidate Radioligands for in Vivo Imaging of the Serotonin Transporter with Positron Emission Tomography
  作者：Jeffrey S. Stehouwer、Nachwa Jarkas、Fanxing Zeng、Ronald J. Voll、Larry Williams、Michael J. Owens、John R. Votaw、Mark M. Goodman

  DOI：10.1021/jm060641q

  日期：2006.11.1

  '-((Z)-2-iodoethenyl)phenyl)nortropane (mZIENT, 1) and 2beta-carbomethoxy-3beta-(3'-((Z)-2-bromoethenyl)phenyl)nortropane (mZBrENT, 2) were synthesized and evaluated for binding to the human serotonin, dopamine, and norepinephrine transporters (SERT, DAT, and NET, respectively) using transfected cells. Both 1 and 2 have a high affinity for the SERT (Ki=0.2 nM) and are approximately 160 times more selective

  2beta-羰甲氧基-3beta-（3'-（（（Z）-2-碘乙烯基）苯基）降冰片烷（mZIENT，1）和2beta-羰甲氧基-3beta-（3'-（（（Z）-2-溴乙烯基）苯基） （mZBrENT，2）合成并使用转染的细胞评估与人血清素，多巴胺和去甲肾上腺素转运蛋白（分别为SERT，DAT和NET）的结合。1和2对SERT的亲和性都很高（Ki = 0.2 nM），对SERT的选择性是DAT的160倍左右。化合物2对NET的亲和力比1高得多，这可能是卤素原子的大小和电负性不同的结果。在具有[11C] 1和[11C] 2的非人类灵长类动物中的MicroPET成像表明，两种示踪剂在体内的行为相似，在富含SERT的大脑区域中观察到了高吸收，并且在注射后约55分钟内达到了峰值吸收。对西酞普兰和哌醋甲酯的追踪研究表明，这种摄取是优先结合SERT的结果。
• Process for synthesizing anhydroecgonine derivative
  申请人：——

  公开号：US20010020096A1

  公开（公告）日：2001-09-06

  The present invention relates to a process for synthesizing an anhydroecgonine derivative without using cocaine as a starting material, and a process for synthesizing a phenyltropane derivative by using said anhydroecgonine derivative as an intermediate for the synthesis. The present invention provides a process for synthesizing an anhydroecgonine derivative which comprises reacting a cycloheptatriene derivative represented by the formula (1): 1 with a primary amine, a salt thereof or ammonia in the presence of a base to obtain an anhydroecgonine derivative, and a process for synthesizing a phenyltropane derivative by using said anhydroecgonine derivative. In the formula (1), n is an integer of 0 or 1; and R 1 is a cyano group in the case of n being 0, and R 1 is selected from an alkyl group and an aralkyl group in the case of n being 1.

  本发明涉及一种无需使用可卡因作为起始物质合成一种无水异可卡因衍生物的方法，以及使用所述无水异可卡因衍生物作为合成中间体合成苯基曲马多衍生物的方法。本发明提供了一种合成无水异可卡因衍生物的方法，包括将式（1）所表示的环庚三烯衍生物与一种一级胺、其盐或氨在碱的存在下反应，以获得一种无水异可卡因衍生物，以及使用所述无水异可卡因衍生物合成苯基曲马多衍生物的方法。在式（1）中，n为0或1的整数；当n为0时，R1为氰基；当n为1时，R1选自烷基和芳基烷基。
• Method of fluorine-18 labelling of tropane derivatives
  申请人：Orphachem

  公开号：EP1925615A1

  公开（公告）日：2008-05-28

  The invention relates to a one-step [18F]radiolabelling process of tropanamine derivatives which are useful for imaging the neuronal dopamine transporter (DAT) with Positron Emission Tomography (PET).

  本发明涉及托烷胺衍生物的一步法[18F]放射性标记工艺，该工艺可用于正电子发射断层扫描（PET）对神经元多巴胺转运体（DAT）进行成像。