(1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-cyclohexane-carboxylic acid propylamide | 1151911-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-cyclohexane-carboxylic acid propylamide
• CAS: 1151911-12-4
• 化学式: C₁₀H₁₉NO₅
• 分子量: 233.265
• InChiKey: XHPCHPXULIXREB-DQUBFYRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.88
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  110.02
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5,7-dihydroxy-2,2-dimethyl-N-propyl-hexahydrobenzo[d][1,3]dioxole-5-carboxamide 在 盐酸 、 水 作用下， 反应 1.0h， 以100%的产率得到(1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-cyclohexane-carboxylic acid propylamide
  参考文献：
  名称：

  [EN] ANTI-INFLAMMATORY QUINIC ACID DERIVATIVES FOR ORAL ADMINISTRATION
  [FR] DÉRIVÉS ANTI-INFLAMMATOIRES DE L'ACIDE QUINIQUE POUR UNE ADMINISTRATION PAR VOIE ORALE

  摘要：

  揭示了一种含有奎尼酸或樟脑酸类似物的化合物，具有抗炎性能。这些化合物适合口服，稳定，并且在抑制NF-kB、抑制白细胞粘附以及抑制其他已知参与炎症性疾病的因子和细胞因子方面表现出显著的功效。

  公开号：

  WO2009062200A1

文献信息

• Anti-Inflammatory Quinic Acid Derivatives for Oral Administration
  申请人：Yates Charles R.

  公开号：US20090234015A1

  公开（公告）日：2009-09-17

  Disclosed are compounds comprising analogs of quinic acids or shikimic acids having anti-inflammatory properties. The compounds are suitable for oral administration, stable, and demonstrate significant efficacy in inhibiting NF-kB, inhibiting leukocyte adhesion, and inhibiting other factors and cytokines known to be involved in inflammatory disease.

  本发明涉及一种具有抗炎性质的类奎尼酸或香豆酸类似物化合物。这些化合物适合口服，稳定，并且在抑制NF-kB，抑制白细胞粘附以及抑制其他已知参与炎症性疾病的因子和细胞因子方面表现出显著的功效。
• Anti-Inflammatory Quinic Acid Derivatives for Radioprotection/Radiomitigation
  申请人：Yates Charles Ryan

  公开号：US20120283331A1

  公开（公告）日：2012-11-08

  Disclosed are methods of use of analogs of quinic acids or shikimic acids for protection from the harmful effects of radiation when administered either prior to radiation exposure, after radiation exposure, or both. These methods are useful for treating humans and animals exposed to radiation and at risk for radiation sickness and/or death as the result of radiation exposure.

  本发明公开了使用奎尼酸或植酸的类似物在辐射暴露之前、之后或两者同时给药时保护人类和动物免受辐射有害影响的方法。这些方法对于治疗暴露于辐射并有辐射病和/或死亡风险的人类和动物非常有用。
• Synthesis and biological evaluation of quinic acid derivatives as anti-inflammatory agents
  作者：Kui Zeng、Karin Emmons Thompson、Charles R. Yates、Duane D. Miller

  DOI：10.1016/j.bmcl.2009.07.096

  日期：2009.9

  Quinic acid (QA) esters found in hot water extracts of Uncaria tomentosa (a.k.a. cat's claw) exert anti-inflammatory activity through mechanisms involving inhibition of the pro-inflammatory transcription factor nuclear factor kappa B (NF-kappa B). Herein, we describe the synthesis and biological testing of novel QA derivatives. Inhibition of NF-kappa B was assessed using A549 (Type 11 alveolar epithelial-like) cells that stably express a secreted alkaline phosphatase (SEAP) reporter driven by an NF-kappa B response element. A549-NF-kappa B cells were stimulated with TNF-alpha (10 ng/mL) in the presence or absence of QA derivative for 18 hours followed by measurement of SEAP activity. Amide substitution at the carboxylic acid position yielded potent inhibitors of NF-kappa B. A variety of modifications to the amide substitution were tolerated with the N-propyl amide derivative being the most potent. Further examination of the SAR demonstrated that acetylation of the hydroxyl groups reduced NF-kappa B inhibitory activity. QA amide derivatives lacked anti-oxidant activity and were found to be neither anti-proliferative nor cytotoxic at concentrations up to 100 mu M. In conclusion, we have discovered a novel series of non-toxic QA amides that potently inhibit NF-kappa B, despite their lack of anti-oxidant activity. Mechanistic studies and pre-clinical efficacy studies in various inflammatory animal models are on-going. (C) 2009 Elsevier Ltd. All rights reserved.
• US8115031B2
  申请人：——

  公开号：US8115031B2

  公开（公告）日：2012-02-14
• US8906965B2
  申请人：——

  公开号：US8906965B2

  公开（公告）日：2014-12-09