(2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate | 737830-25-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate
• 英文别名: (2S,3S)-2-[[6,7-bis(carboxymethoxy)-2-oxochromen-4-yl]methoxycarbonylamino]-3-phenylmethoxybutanedioic acid
• CAS: 737830-25-0
• 化学式: C₂₆H₂₃NO₁₅
• 分子量: 589.466
• InChiKey: QWJYKUWQFDYHBY-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  242
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  BCMCM-OH 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2S,3S)-3-benzyloxy-N-{[6,7-bis(carboxymethoxy)coumarin-4-yl-methoxy]carbonyl}aspartate
  参考文献：
  名称：

  Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker

  摘要：

  L-threa-beta-Benzyloxyaspartate (L-TBOA) and (2S,3S)-3-{3-[4-(trifluoromethyl)benzoylamino]benzyloxy}aspartate (L-TFB-TBOA) are potent nontransportable blockers for glutamate transporters. We synthesized a carbamate-type coumarin derivative of L-TBOA 3a as a caged blocker and compared 3a with the corresponding ester-type analogs 1. The carbamate 3a was less sensitive to photolysis than the ester I but was more stable in the aqueous solution. The [6,7-bis(carboxymethoxy)-coumarin-4yl]methylcarbonyl (BCMCMC) group exhibited good results both in photoreactivity and stability. Therefore, we examined photolysis of N-BCMCMC-TBOA 3b and N-BCMCMC-TFB-TBOA 4, which immediately released blockers to show glutamate uptake inhibition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.011

文献信息

• (BETA)-BENZYLOXYASPARTATE DERIVATIVES WITH PHOTOSENSITIVE GROUPS
  申请人：Suntory Holdings Limited

  公开号：EP1628951B1

  公开（公告）日：2010-05-26
• B-BENZYLOXYASPARTATE DERIVATIVES WITH PHOTOSENSITIVE GROUPS
  申请人：Shimamoto Keiko

  公开号：US20070158175A1

  公开（公告）日：2007-07-12

  The present invention relates to photosensitive derivatives of optically active L-threo-β-benzyloxyaspartate or its benzene ring-substituted analogs, represented by the following formula (1) or (2): (1) (2) wherein R 1 represents hydrogen atom, amino group, straight or branched lower aliphatic acylamino group optionally substituted at the acyl group portion, alicyclic acylamino group or aromatic acylamino group optionally having a substituent on the aromatic ring, R 2 represents hydrogen atom or one or more straight or branched optionally substituted lower aliphatic alkyloxy groups on the benzene ring, R3 represents hydrogen atom, methyl group or carboxyl group, and R4 and R5 each represent hydrogen atom, hydroxyl group, straight or branched lower alkyloxy group optionally substituted at the alkyl portion, amino group, straight or branched lower alkyl-substituted amino group, or a halogen atom, which upon photoirradiation can produce compounds exhibiting a function of suppressing the glutamate uptake activity of L-glutamate transporters.
• US7622499B2
  申请人：——

  公开号：US7622499B2

  公开（公告）日：2009-11-24
• Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker
  作者：Kiyo Takaoka、Yoshiro Tatsu、Noboru Yumoto、Terumi Nakajima、Keiko Shimamoto

  DOI：10.1016/j.bmc.2004.04.011

  日期：2004.7

  L-threa-beta-Benzyloxyaspartate (L-TBOA) and (2S,3S)-3-3-[4-(trifluoromethyl)benzoylamino]benzyloxy}aspartate (L-TFB-TBOA) are potent nontransportable blockers for glutamate transporters. We synthesized a carbamate-type coumarin derivative of L-TBOA 3a as a caged blocker and compared 3a with the corresponding ester-type analogs 1. The carbamate 3a was less sensitive to photolysis than the ester I but was more stable in the aqueous solution. The [6,7-bis(carboxymethoxy)-coumarin-4yl]methylcarbonyl (BCMCMC) group exhibited good results both in photoreactivity and stability. Therefore, we examined photolysis of N-BCMCMC-TBOA 3b and N-BCMCMC-TFB-TBOA 4, which immediately released blockers to show glutamate uptake inhibition. (C) 2004 Elsevier Ltd. All rights reserved.