Methyl 1-(tert-butoxycarbonylamino)-3-oxocyclopentanecarboxylate | 191111-14-5

• 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: Methyl 1-(tert-butoxycarbonylamino)-3-oxocyclopentanecarboxylate
• 英文别名: methyl 1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxocyclopentane-1-carboxylate
• CAS: 191111-14-5
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: UQSBSMLCPAEGPU-UHFFFAOYSA-N

物化性质

• 沸点：
  371.1±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 1-(tert-butoxycarbonylamino)-3-oxocyclopentanecarboxylate 在 四(三苯基膦)钯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 1-tert-Butoxycarbonylamino-3-(diethoxy-phosphoryl)-cyclopent-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis, molecular modeling and preliminary biological evaluation of 1-amino-3-phosphono-3-cyclopentene-1-carboxylic acid and 1-amino-3-phosphono-2-cyclopentene-1-carboxylic acid, two novel agonists of metabotropic glutamate receptors of group III

  摘要：

  On the basis of a pharmacophore definition of mGlu(4) agonists, the two novel semi-rigid derivatives 12 and 13 were designed and synthesized. The preliminary biological evaluation demonstrated that both compounds interact with hmGlu(4a), while ineffective at group II receptor subtypes. In particular. derivative 13 is a full hmGlu(4a) agonist with an EC50= 17 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00247-x
• 作为产物：
  描述：

  1-(Methoxycarbonyl)cyclopent-3-ene-1-carboxylic acid 在 氯化亚砜 、 sodium azide 、 三氟化硼四氢呋喃络合物 、 chromium trioxide-pyridine complex 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 24.5h， 生成 Methyl 1-(tert-butoxycarbonylamino)-3-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Synthesis, molecular modeling and preliminary biological evaluation of 1-amino-3-phosphono-3-cyclopentene-1-carboxylic acid and 1-amino-3-phosphono-2-cyclopentene-1-carboxylic acid, two novel agonists of metabotropic glutamate receptors of group III

  摘要：

  On the basis of a pharmacophore definition of mGlu(4) agonists, the two novel semi-rigid derivatives 12 and 13 were designed and synthesized. The preliminary biological evaluation demonstrated that both compounds interact with hmGlu(4a), while ineffective at group II receptor subtypes. In particular. derivative 13 is a full hmGlu(4a) agonist with an EC50= 17 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00247-x

文献信息

• [EN] AMINO ACID ANALOGS FOR TUMOR IMAGING<br/>[FR] ANALOGUES D'ACIDES AMINES POUR L'IMAGERIE DES TUMEURS
  申请人：EMORY UNIVERSITY

  公开号：WO1997017092A1

  公开（公告）日：1997-05-15

  (EN) The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is [18F]-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an $g(a)-amino acid moiety attached to either a four-, five-, or a six-member carbon-chain ring. In addition, the invention features analogs of $g(a)-aminoisobutyric acid.(FR) L'invention concerne de nouveaux composés acides aminés servant à détecter et évaluer les tumeurs dans le cerveau et d'autres parties du corps. Ces composés combinent les propriétés avantageuses des acides 1-amino-cycloalkyl-1-carboxyliques, en particulier leur assimilation rapide et leur persistance dans les tumeurs, avec les propriétés des substituants halogènes, en particulier de certains isotopes utiles tels que le fluor 18, l'iode 123, l'iode 125, l'iode 131, le brome 75, le brome 76, le brome 77 et le brome 82. Selon un aspect, l'invention concerne des composés acides aminés ayant une spécificité très élevée pour les sites visés quand ils sont administrés à un sujet in vivo. Les composés acides aminés préférés présentent une sélectivité sites visés/sites non visés d'au moins 5:1, ils sont stables in vivo et se retrouvent dans le site visé 1 heure après l'administration. Un acide aminé particulièrement préféré est l'acide [18F] -1-amino-3-fluorocyclobutane-1-carboxylique. Selon un autre aspect, l'invention concerne des compositions pharmaceutiques constituées d'un fragment $g(a)-aminoacide fixé à un cycle ayant une chaîne de quatre, cinq ou six atomes de carbone. En outre, l'invention concerne des analogues de l'acide $g(a)-aminoisobutyrique.

  本发明提供了新型氨基酸化合物，用于检测和评估脑和身体肿瘤。这些化合物结合了1-氨基环烷基-1-羧酸的优越性质，即它们在肿瘤中的快速摄取和长时间保留，以及卤素取代基的性质，包括某些有用的卤素同位素，如氟-18、碘-123、碘-125、碘-131、溴-75、溴-76、溴-77和溴-82。在一个方面，本发明涉及在体内给予受试者的具有高靶点特异性的氨基酸化合物。优选的氨基酸化合物显示出至少5:1的靶点与非靶点比率，在体内稳定，并在给药后1小时内大量定位于靶点。特别优选的氨基酸化合物是[18F]-1-氨基-3-氟环丁基-1-羧酸（FACBC）。在另一个方面，本发明涉及由$g（a）-氨基酸基团与四、五或六元碳链环之一连接而成的药物组成物。此外，本发明还涉及$g（a）-氨基异丁酸的类似物。
• Synthesis, molecular modeling and preliminary biological evaluation of 1-amino-3-phosphono-3-cyclopentene-1-carboxylic acid and 1-amino-3-phosphono-2-cyclopentene-1-carboxylic acid, two novel agonists of metabotropic glutamate receptors of group III
  作者：Laura Amori、Gabriele Costantino、Maura Marinozzi、Roberto Pellicciari、Fabrizio Gasparini、Peter J Flor、Rainer Kuhn、Ivo Vranesic

  DOI：10.1016/s0960-894x(00)00247-x

  日期：2000.7

  On the basis of a pharmacophore definition of mGlu(4) agonists, the two novel semi-rigid derivatives 12 and 13 were designed and synthesized. The preliminary biological evaluation demonstrated that both compounds interact with hmGlu(4a), while ineffective at group II receptor subtypes. In particular. derivative 13 is a full hmGlu(4a) agonist with an EC50= 17 mu M. (C) 2000 Elsevier Science Ltd. All rights reserved.