2-oxoadamantane-1-carboxylic acid | 40556-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxoadamantane-1-carboxylic acid
• 英文别名: adamantanone-2-carboxylic acid；2-oxo-adamantane-1-carboxylic acid；2-Keto-adamantan-1-carbonsaeure；2-Keto-1-adamantancarbonsaeure；2-Oxoadamantan-1-carbonsaeure；Adamantan-2-on-3-carbonsaeure
• CAS: 40556-86-3
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: CREOOLZKVAFMCX-UHFFFAOYSA-N

物化性质

• 沸点：
  367.6±25.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxoadamantane-1-carboxylic acid 在 氯化亚砜 作用下， 反应 2.0h， 以100%的产率得到2-Oxo-1-adamantancarbonsaeurechlorid
  参考文献：
  名称：

  Synthesis of Adamantane Derivatives; 48¹. Synthesis of Some Novel 1,2-Fused Adamantane Azaheterocycles via 2-Oxoadamant-1-yl Isocyanate

  摘要：

  DOI：

  10.1055/s-1980-29059
• 作为产物：
  描述：

  4-(epoxymethylene)protoadamantane 在 Jones reagent 、 硫酸 作用下， 以 水 为溶剂， 反应 1.25h， 生成 2-oxoadamantane-1-carboxylic acid
  参考文献：
  名称：

  Anti-allodynic effect of 2-(aminomethyl)adamantane-1-carboxylic acid in a rat model of neuropathic pain: A mechanism dependent on CaV2.2 channel inhibition

  摘要：

  Neuropathic pain is a serious physical disabling condition resulting from lesion or dysfunction of the peripheral sensory nervous system. Despite the fact that the mechanisms underlying neuropathic pain are poorly understood, the involvement of voltage-gated calcium (Ca-V) channels in its pathophysiology has justified the use of drugs that bind the Ca-V channel alpha(2)delta auxiliary subunit, such as gabapentin (GBP), to attain analgesic and anti-allodynic effects in models involving neuronal sensitization and nerve injury. GBP binding to alpha(2)delta inhibits nerve injury-induced trafficking of the alpha(1) pore forming subunits of Ca-V channels, particularly of the N-type, from the cytoplasm to the plasma membrane of pre-synaptic terminals in dorsal root ganglion neurons and dorsal horn spinal neurons. In the search for alternative forms of treatment, in this study we describe the synthesis and pharmacological profile of a GABA derivative, 2-aminoadamantane-1-carboxylic acid (GZ4), which displays a close structure-activity relationship with GBP. Behavioral assessment using von Frey filament stimuli showed that GZ4 treatment reverted mechanical allodynia/hyperalgesia in an animal model of spinal nerve ligation-induced neuropathic pain. In addition, using the patch clamp technique we show that GZ4 treatment significantly decreased whole-cell currents through N-type Ca-V channels heterologously expressed in HEK-293 cells. Interestingly, the behavioral and electrophysiological time course of GZ4 actions reflects that its mechanism of action is similar but not identical to that of GBP. While GBP actions require at least 24 h and imply uptake of the drug, which suggests that the drug acts mainly intracellularly affecting channels trafficking to the plasma membrane, the faster time course (1-3 h) of GZ4 effects suggests also a direct inhibition of Ca2+ currents acting on cell surface channels. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.006

文献信息

• Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide
  作者：Leo Mandić、Kata Mlinarić-Majerski、Axel G. Griesbeck、Nikola Basarić

  DOI：10.1002/ejoc.201600491

  日期：2016.9

  derivatives 3–6 underwent a photoinduced electron transfer (PET) and decarboxylation reaction sequence, most probably through a triplet excited state. The decarboxylations of the β-amino acid derivatives were succeeded by cyclization reactions that afforded complex polycyclic molecules with potential biological interest. The adamantyl radical that is produced by the photoinduced decarboxylation could be

  合成了由邻苯二甲酰亚胺（即 3-6）活化的金刚烷 α-、β-和 δ-氨基酸，并研究了它们的光化学反应性。氨基酸衍生物 3-6 经历了光诱导电子转移 (PET) 和脱羧反应序列，最有可能是通过三重激发态。β-氨基酸衍生物的脱羧通过环化反应成功，提供了具有潜在生物学意义的复杂多环分子。光诱导脱羧产生的金刚烷基自由基可以被烯烃或氧捕获，分别传递加合物或醇。在丙酮敏化条件下（量子产率，Φ = 0.02-0.5），光脱羧过程比直接激发更有效，并且反应性取决于衍生物的电子供体（羧酸盐）和受体（三重激发态的邻苯二甲酰亚胺）之间的链长（分子内距离）。不同自由基的形成，即 1- 或 2-金刚烷基中间体，可能不会影响脱羧的整体速率本报告提供了对光脱羧的更好理解和分子系统的合理设计以进行光诱导脱羧和环化反应。
• 3,7-disubstituted bicyclo[3.3.1]nonanes—III
  作者：J.A. Peters、J.M. Van Der Toorn、H. Van Bekkum

  DOI：10.1016/0040-4020(75)80226-2

  日期：1975.1

  The conformation of bicyclo[3.3.1]nonane-3α,7α-dicarboxylic acid and its dimethyl ester has been studied by comparing 1H NMR and 13C NMR spectra of these compounds with those of some model 3,7-disubstituted bicyclo[3.3.1]nonanes, fixed in a single conformation by the use of adamantane as an integrated holding group or by means of suitable substitution. It is shown that the dicarboxylic acid and its

  通过比较这些化合物的1 H NMR和13 C NMR谱图与某些模型的3,7-二取代双环[3.3]谱图，研究了双环[3.3.1]壬烷-3α，7α-二羧酸及其二甲酯的构象。.1]壬烷，通过使用金刚烷作为一个整体的保留基团或通过适当的取代固定在一个构象中。结果表明，二羧酸及其二甲基酯主要以两个快速相互转化（相同）的椅形结构存在，并且环明显扁平。双人船构型的人口似乎很少。
• N-Adamantane-substituted tetrapeptide amides
  申请人：G. D. Searle & Co.

  公开号：US04273704A1

  公开（公告）日：1981-06-16

  N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.

  本文披露了N-金刚烷取代的四肽酰胺及其药理学上可接受的盐。这些化合物是脑啡肽的类似物，其中第5位的蛋氨酸或亮氨酸被金刚烷酰胺替代，第2位的甘氨酸被各种氨基酸残基替代。选项地，第1位的酪氨酸和第4位的苯丙氨酸可以被各种氨基酸残基替代。这些化合物在鸦片受体位点表现出激动剂活性，并可用作镇痛剂。
• Xanthine derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0619316A1

  公开（公告）日：1994-10-12

  There is provided a novel xanthine Compound(I) wherein R¹ and R² are the same or different and each represent hydroxy-substituted, oxo-substituted or unsubstituted lower alkyl, Y is a single bond or alkylene, and Q is wherein R³ and R⁴ are the same or different and each represent hydrogen or hydroxy, n is 0 or 1; provided that when both of R³ and R⁴ are hydrogen, at least one of R¹ and R² is hydroxy-substituted or oxo-substituted lower alkyl; or a pharmaceutically acceptable salt thereof. The xanthine compound has adenosine A₁ receptor antagonizing activity, and thus shows diuretic effect, renal-protecting effect, bronchodilatory effect, cerebral function improving effect and anti-dementia effect.

  提供了一种新型黄嘌呤化合物(I) 其中 R¹ 和 R² 相同或不同，各自代表羟基取代、氧代取代或未取代的低级烷基，Y 为单键或亚烷基，Q 为 其中 R³ 和 R⁴ 相同或不同且各自代表氢或羟基，n 为 0 或 1；但当 R³ 和 R⁴ 均为氢时，R¹ 和 R² 中至少有一个是羟基取代的或氧化取代的低级烷基；或其药学上可接受的盐。 黄嘌呤化合物具有腺苷 A₁受体拮抗活性，因此具有利尿作用、肾保护作用、支气管扩张作用、脑功能改善作用和抗痴呆作用。
• 4-Oxatricyclo(4.3.1.1-3,8)undecan-5-one derivatives and process for producing the same
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1081150A1

  公开（公告）日：2001-03-07

  A 4-oxatricyclo[4.3.1.13,8]undecan-5-one derivative is shown by the following formula (1): wherein R is a hydrogen atom or a (meth)acryloyl group, and carbon atoms constituting a ring may have a substituent in addition to the substituents indicated in the formula. This compound is a novel 4-oxatricyclo[4.3.1.13,8]undecan-5-one derivative having a hydroxyl group or a (meth)acryloyloxy group at the 1-position.

  4-oxatricyclo[4.3.1.13,8]undecan-5-one 衍生物如下式（1）所示： 其中 R 是氢原子或（甲基）丙烯酰基，而构成环的碳原子除了具有式中所示的取代基外，还可以具有一个取代基。该化合物是一种新型 4-氧杂三环[4.3.1.13,8]十一烷-5-酮衍生物，在 1 位上具有羟基或（甲基）丙烯酰氧基。