(1R,4S,6R)-7-氧杂双环[2.2.1]庚烷-6-羧酸 | 19800-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: (1R,4S,6R)-7-氧杂双环[2.2.1]庚烷-6-羧酸
• 英文名称: (+/-)-endo-7-oxabicyclo<2.2.1>-heptane-2-carboxylic acid
• 英文别名: (rac-endo)-7-oxabicyclo-[2.2.1]heptane-2-carboxylic acid；(+/-)-endo-7-oxabicyclo[2.2.1]-heptane-2-carboxylic acid；exo-7-Oxabicyclo(2.2.1)heptane-2-carboxylic acid；(1R,2R,4S)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 19800-01-2；38263-55-7；38263-56-8；64589-27-1
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: UYLYISCHTFVYHN-KVQBGUIXSA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  290.7±23.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S,6R)-7-氧杂双环[2.2.1]庚烷-6-羧酸 在 palladium on activated charcoal 硫酸 、 硼烷 、 氢气 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 80.0 ℃ 、103.42 kPa 条件下， 反应 73.75h， 生成 DL-(1,5/4)-1-O-methyl-5-C-hydroxymethyl-1,4-cyclohexanediol
  参考文献：
  名称：

  Spohr, Ulrike; Paszkiewicz-Hnatiw, Eugenia; Morishima, Naohiko, Canadian Journal of Chemistry, 1992, vol. 70, # 1, p. 254 - 271

  摘要：

  DOI：
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 以89%的产率得到
  参考文献：
  名称：

  TAKAYAMA, HIROMITSU;IYOBE, AKIRA;KOIZUMI, TORU, J. CHEM. SOC. CHEM. COMMUN., 1986, N 10, 771-772

  摘要：

  DOI：

文献信息

• Pseudo-sugars. 3. Alternative Synthesis of Penta-<i>N</i>,<i>O</i>-acetyl-DL-validamine and Its Analogs
  作者：Seiichiro Ogawa、Isamu Kasahara、Tetsuo Suami

  DOI：10.1246/bcsj.52.118

  日期：1979.1

  Dl-Validamine and its amino deoxy and deoxy analogs were synthesized as the acetyl derivatives from endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid, the Diels-Alder adduct of acrylic acid and furan.

  Dl-Validamine及其氨基脱氧和脱氧类似物是从内-7-氧杂双环[2.2.1]庚-5-烯-2-羧酸（丙烯酸和呋喃的Diels-Alder加合物）合成的乙酰衍生物。
• HETERO BICYCLIC CARBOXAMIDE DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS
  申请人：Schnute Mark E.

  公开号：US20110009435A1

  公开（公告）日：2011-01-13

  The present invention relates to compounds of Formula I and pharmaceutically acceptable salts thereof, processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds as anti-inflammatory agents.

  本发明涉及公式I化合物及其药学上可接受的盐、制备该化合物的方法、制备中间体以及含有该化合物的组合物和该化合物作为抗炎药物的用途。
• Discovery of a Novel Small-Molecule Modulator of C–X–C Chemokine Receptor Type 7 as a Treatment for Cardiac Fibrosis
  作者：Elnaz Menhaji-Klotz、Kevin D. Hesp、Allyn T. Londregan、Amit S. Kalgutkar、David W. Piotrowski、Markus Boehm、Kun Song、Tim Ryder、Kevin Beaumont、Rhys M. Jones、Karen Atkinson、Janice A. Brown、John Litchfield、Jun Xiao、Daniel P. Canterbury、Kristen Burford、Benjamin A. Thuma、Chris Limberakis、Wenhua Jiao、Scott W. Bagley、Saket Agarwal、Danielle Crowell、Stephen Pazdziorko、Jessica Ward、David A. Price、Valerie Clerin

  DOI：10.1021/acs.jmedchem.8b00190

  日期：2018.4.26

  C-X-C chemokine receptor type 7 (CXCR7) is involved in cardiac and immune pathophysiology. We report the discovery of a novel 1,4-diazepine CXCR7 modulator, demonstrating for the first time the role of pharmacological CXCR7 intervention in cardiac repair. Structure activityrelationship (SAR) studies demonstrated that a net reduction in lipophilicity (log D) and an incorporation of saturated ring systems yielded compounds with good CXCR7 potencies and improvements in oxidative metabolic stability in human-liver microsomes (HLM). Tethering an ethylene amide further improved the selectivity profile (e.g., for compound 18, CXCR7 K-i = 13 nM, adrenergic alpha la K-b > 10 000 nM, and adrenergic beta 2 K-b > 10 000 nM). The subcutaneous administration of 18 in mice led to a statistically significant increase in circulating concentrations of plasma stromal-cell-derived factor la (SDF-1 alpha) of approximately 2-fold. Chronic dosing of compound 18 in a mouse model of isoproterenol-induced cardiac injury further resulted in a statistically significant reduction of cardiac fibrosis.
• [EN] HETERO BICYCLIC CARBOXAMIDE DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS<br/>[FR] DÉRIVÉS CARBOXAMIDES HÉTÉRO-BICYCLIQUES ET LEUR UTILISATION PHARMACEUTIQUE ET COMPOSITIONS
  申请人：PFIZER

  公开号：WO2008149191A1

  公开（公告）日：2008-12-11

  [EN] The present invention relates to compounds of Formula (I)I and pharmaceutically acceptable salts thereof, processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds as anti-inflammatory agents.
  [FR] La présente invention concerne des composés représentés par la formule (I)I et des sels pharmaceutiquement acceptables de ceux-ci, des procédés de préparation desdits composés, des intermédiaires utilisés pour leur préparation et des compositions les contenant, ainsi que l'utilisation desdits composés en tant qu'agents anti-inflammatoires.
• [EN] PYRIMIDINE AND PYRIDINE DERIVATIVES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS<br/>[FR] DÉRIVÉS DE PYRIMIDINE ET DE PYRIDINE ET LEUR UTILISATION PHARMACEUTIQUE ET LEURS COMPOSITIONS
  申请人：PFIZER

  公开号：WO2009016498A1

  公开（公告）日：2009-02-05

  The prsent invention relates to compounds of Formula (I) and pharmaceutically acceptable salts thereof, processes for the preparation of, intermediates used in the preparation of, and compositions containing such compounds and the uses of such compounds as anti-inflammatory agents.