cis-ACBD,cis-1-Aminocyclobutane-1,3-dicarboxylicacid | 73550-55-7

• 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: cis-ACBD,cis-1-Aminocyclobutane-1,3-dicarboxylicacid
• 英文别名: Cis-ACBD；cis-1-aminocyclobutane-1,3-dicarboxylic acid；1-amino-1,3-dicarboxycyclobutane；trans-2,4-methanoglutamic acid；cis-2,4-methanoglutamic acid；2-methanoglutamic acid
• CAS: 73550-55-7
• 化学式: C₆H₉NO₄
• mdl: MFCD00153764
• 分子量: 159.142
• InChiKey: GGMYWPBNZXRMME-MYNUVTBMSA-N

物化性质

• 沸点：
  288.1±40.0 °C(Predicted)
• 密度：
  1.568±0.06 g/cm3(Predicted)
• 溶解度：
  1eq 中可溶解至 100 毫升氢氧化钠

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  100.62
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  cis-methyl 1-(benzoylamino)-1-(pentamethylenecarbamoyl)cyclobutane-3-carboxylate 在 盐酸 作用下， 反应 24.0h， 以85%的产率得到cis-ACBD,cis-1-Aminocyclobutane-1,3-dicarboxylicacid
  参考文献：
  名称：

  Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives

  摘要：

  A range of cis- and trans-3-substituted 1-aminocyclobutane-1-carboxylic acids has been synthesized and evaluated for antagonism at excitatory amino acid receptor sites and for anticonvulsant activity. Potent and selective antagonist:activity at N-methyl-D-aspartate (NMDA) receptor sites in neonatal rat motoneurones was shown by compounds in which the 3-substituent was, or contained, a 2'-carboxyethyl or 2'-phosphonoethyl moiety. Substances 4b, 24, 35, and 40 were more potent than the standard NMDA receptor antagonist, D-2-amino-5-phosphonopentanoate (D-AP5) as NMDA antagonists in this preparation, and about equipotent with [3-(+/-)-2-carboxypiperazin-4-yl)-1-propyl]phosphonate (CPP). Anticonvulsant activity, as assessed following intracerebroventricular injection into audiogenic DBA/2 mice, generally paralleled NMDA receptor antagonist activity.

  DOI：

  10.1021/jm00051a005

文献信息

• Synthesis and activity of a potent N-methyl-D-aspartic acid agonist, trans-1-aminocyclobutane-1,3-dicarboxylic acid, and related phosphonic and carboxylic acids
  作者：Robin D. Allan、Jane R. Hanrahan、Trevor W. Hambley、Graham A. R. Johnston、Kenneth N. Mewett、Ann D. Mitrovic

  DOI：10.1021/jm00172a036

  日期：1990.10

  preparation or as antagonist of the actions of the selective agonists NMDA, quisqualic acid, and kainic acid. The chain-elongated glutamate derivatives with potential antagonist activity proved to be weak and frequently nonselective antagonists in this assay. The most noteworthy result was that trans isomer 7b was a very potent agonist, approximately 20 times more active than NMDA at NMDA receptors, while the

  我们报告了一系列3-羧基-，3-（羧甲基）-，3-（ω-膦酰基烷基）-1-氨基环丁烷-1-羧酸的合成，以评估在兴奋性氨基酸受体上作为神经传递的激动剂或拮抗剂，特别是N-甲基-D-天冬氨酸（NMDA）受体。将该化合物评估为对大鼠大脑皮质楔形制剂的去极化能力的激动剂，或作为选择性激动剂NMDA，喹鲨酸和海藻酸的拮抗剂。具有潜在拮抗剂活性的链延长的谷氨酸衍生物被证明是弱的，并且在该测定中经常是非选择性拮抗剂。最值得注意的结果是反式异构体7b是一种非常有效的激动剂，在NMDA受体上的活性是NMDA的20倍左右，而顺式异构体的活性是NMDA的1/3。
• Regiospecific additions of hydrazoic acid and benzylamine to 1-(arylsulfonyl)bicyclo[1.1.0]Butanes. Application to the synthesis of cis and trans 2,7-methanoglutamic acids
  作者：Yehiel Gaoni

  DOI：10.1016/s0040-4039(00)80361-5

  日期：——

  Addition of hydrazoic acid or benzylamine to 1-(arylsulfonyl) bicyclobutanes introduces the nitrogen nucleophlle at position 3 of the derived cyclobutane, even when a carboxyl derivative is present at this position as a second activating group. Precursors of α-amino cyclobutane carboxylic acids may thus be obtained and these can be further transformed to the title diacids via carbonylation α to the

  即使将羧基衍生物作为第二活化基团存在于该位置的环丁烷的3位上，向1（芳基磺酰基）双环丁烷中添加氢唑酸或苄基胺也可在该位置上引入氮原子。因此可以得到α-氨基环丁烷羧酸的前体，并且可以通过将α羰基化成砜并还原，将它们进一步转化为标题二酸。
• Derivatives of succinic and glutaric acids and analogs thereof useful as inhibitors of phex
  申请人：Gravel Denis

  公开号：US20060135480A1

  公开（公告）日：2006-06-22

  The present invention relates to derivatives of succinic and glutaric acids and analogues thereof, having the following general formula (I), useful as inhibitors of PHEX. These derivatives are useful for promoting generation of bone mass and treating or preventing diseases or conditions associated with a phosphate metabolism defect. Methods for preparation and intermediates are also disclosed.

  本发明涉及琥珀酸和戊二酸的衍生物及其类似物，具有以下一般式（I），可用作PHEX的抑制剂。这些衍生物有助于促进骨量的生成，并治疗或预防与磷酸盐代谢缺陷相关的疾病或病症。本发明还公开了制备方法和中间体。
• Derivatives of succinic and glutaric acids and analogs thereof useful as inhibitors of PHEX
  申请人：Gravel Denis

  公开号：US20060287280A1

  公开（公告）日：2006-12-21

  The present invention relates to derivatives of succinic and glutaric acids and analogues thereof, having the following general formula: useful as inhibitors of PHEX. These derivatives are useful for promoting generation of bone mass and treating or preventing diseases or conditions associated with a phosphate metabolism defect. Methods for preparation and intermediates are also disclosed.

  本发明涉及琥珀酸和戊二酸及其类似物的衍生物，其具有以下一般式：用作PHEX的抑制剂。这些衍生物有助于促进骨量的生成，并用于治疗或预防与磷酸盐代谢缺陷有关的疾病或病况。本发明还公开了制备方法和中间体。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。