3-(环戊基氧基)苯甲酸 | 158860-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(环戊基氧基)苯甲酸
• 英文名称: 3-(cyclopentyloxy)benzoic acid
• 英文别名: 3-cyclopentyloxybenzoic acid
• CAS: 158860-99-2
• 化学式: C₁₂H₁₄O₃
• mdl: MFCD09735105
• 分子量: 206.241
• InChiKey: GFTZDGGMZKVKKN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.6±15.0 °C(Predicted)
• 密度：
  1.207

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  3-(环戊基氧基)苯甲酸 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 3-Cyclopentyloxybenzoyl chloride
  参考文献：
  名称：

  Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs

  摘要：

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.

  DOI：

  10.1021/jm00037a021
• 作为产物：
  描述：

  3-环戊基氧基-苯甲醛 在 sodium chlorite 、 氨基磺酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 3-(环戊基氧基)苯甲酸
  参考文献：
  名称：

  Selective Type IV Phosphodiesterase Inhibitors as Antiasthmatic Agents. The Syntheses and Biological Activities of 3-(Cyclopentyloxy)-4-methoxybenzamides and Analogs

  摘要：

  The syntheses and biological activities of a number of benzamide derivatives, designed from rolipram, which are selective inhibitors of cyclic AMP-specific phosphodiesterase (PDE IV), are described. The effects of changes to the alkoxy groups, amide linkage, and benzamide N-phenyl ring on the inhibition of the cytosolic PDE IV from pig aorta have been investigated. As a result, some highly potent and selective PDE IV inhibitors have been identified. The most potent compounds have been further evaluated for their inhibitory potencies against PDE IV obtained from and superoxide O-2(-) generation from guinea pig eosinophils in vitro. Selected compounds have also been examined for their activities in inhibiting histamine-induced bronchospasm in anaesthetized guinea pigs. 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide (15j) showed exceptional potency in all tests and may have therapeutic potential in the treatment of asthma.

  DOI：

  10.1021/jm00037a021

文献信息

• Orally Available Soluble Epoxide Hydrolase/Phosphodiesterase 4 Dual Inhibitor Treats Inflammatory Pain
  作者：René Blöcher、Karen M. Wagner、Raghavender R. Gopireddy、Todd R. Harris、Hao Wu、Bogdan Barnych、Sung Hee Hwang、Yang K. Xiang、Ewgenij Proschak、Christophe Morisseau、Bruce D. Hammock

  DOI：10.1021/acs.jmedchem.7b01804

  日期：2018.4.26

  enhanced analgesic efficacy between soluble epoxide hydrolase (sEH) and phosphodiesterase 4 (PDE4) inhibitors, we designed, synthesized and characterized 21 novel sEH/PDE4 dual inhibitors. The best of these displayed good efficacy in in vitro assays. Further pharmacokinetic studies of a subset of four selected compounds led to the identification of a bioavailable dual inhibitor N-(4-methoxy-2-(tri

  受先前发现的可溶性环氧化物水解酶 (sEH) 和磷酸二酯酶 4 (PDE4) 抑制剂增强镇痛功效的启发，我们设计、合成并表征了 21 种新型 sEH/PDE4 双重抑制剂。其中最好的在体外试验中显示出良好的功效。对四种选定化合物的子集的进一步药代动力学研究导致鉴定出生物可利用的双重抑制剂N -(4-甲氧基-2-(三氟甲基)苄基)-1-丙酰哌啶-4-甲酰胺 ( MPPA )。在脂多糖诱导的炎症性疼痛大鼠模型中，口服 3 mg/kg 后，血液中的MPPA迅速增加（ T max = 30 分钟；C max = 460 nM），并减少炎症疼痛，且起效迅速，与血液水平相关4小时的时间过程。此外，MPPA不会改变患有炎性疼痛的大鼠的自我激励探索或对照大鼠的戒断潜伏期。
• [EN] ORALLY AVAILABLE SEH/PDE4 DUAL INHIBITORS<br/>[FR] INHIBITEURS DOUBLES SEH/PDE4 DISPONIBLES PAR VOIE ORALE
  申请人：UNIV CALIFORNIA

  公开号：WO2019079609A1

  公开（公告）日：2019-04-25

  Provided herein are novel bioavailable dual inhibitors capable of inhibiting both soluble epoxide hydrolase (sEH) and phosphodiesterase 4 (PDE4), and methods of using the same.

  本文提供了一种新颖的生物可利用的双重抑制剂，能够抑制可溶性环氧水解酶（sEH）和磷酸二酯酶4（PDE4），以及使用这些方法。
• N-terminal modified cyclopeptidic mimetics of ApolloTBM as inhibitors of TRF2
  作者：Xia Chen、Yao Dong、Tianyue Guo、Chao-Yie Yang、Yong Chen、Haiying Sun

  DOI：10.1016/j.bmcl.2020.127401

  日期：2020.11

  compounds which can bind to the TRFH domain of TRF2 and block the interactions between TRF2 and its associated proteins is crucial for elucidating the molecular mechanisms of these protein–protein interactions. Using a previously identified peptidic mimetic of ApolloTBM as a lead compound, we designed and synthesized a series of novel TRF2 inhibitors by non-peptidic modifications of the N-terminal residues

  端粒重复序列结合因子2（TRF2）在保护端粒免于被DNA断裂识别中起重要作用。TRF2通过其TRF同源性（TFRH）域将大量辅助蛋白募集到端粒中，从而部分地发挥其端粒保护功能。鉴定可与TRF2的TRFH结构域结合并阻断TRF2及其相关蛋白之间相互作用的小分子化合物，对于阐明这些蛋白与蛋白相互作用的分子机制至关重要。使用先前鉴定的Apollo TBM肽模拟物作为先导化合物，我们通过N的非肽修饰设计并合成了一系列新型TRF2抑制剂-末端残基。这些化合物可以保持与TRF2的结合亲和力，但与前导化合物相比，其肽段特性大大降低。
• Amide derivatives
  申请人：Brown S. Dearg

  公开号：US20050245551A1

  公开（公告）日：2005-11-03

  The invention concerns amide derivatives of Formula (Ia) wherein X is —NHCO— or —CONH—; m is 0-3; R 1 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino, carboxy and carbamoyl; n is 0-2; R 2 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino and carboxy; R 3 is hydrogen, halogeno, (1-6C)alkyl or (1-6C)alkoxy; q is 0-4; and Q is a group such as aryl, aryloxy, aryl-(1-6C)alkoxy, arylamino and N -(1-6C)alkyl-arylamino; or pharmaceutically-acceptable salts or in-vivo-cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.

  本发明涉及式(Ia)的酰胺衍生物，其中X为—NHCO—或—CONH—；m为0-3；R1为羟基、卤代、三氟甲基、氰基、巯基、硝基、氨基、羧基和氨基甲酰基等基团；n为0-2；R2为羟基、卤代、三氟甲基、氰基、巯基、硝基、氨基和羧基等基团；R3为氢、卤代、(1-6C)烷基或(1-6C)烷氧基；q为0-4；Q为芳基、芳氧基、芳基-(1-6C)烷氧基、芳基氨基和N-(1-6C)烷基-芳基氨基等基团；或其药学上可接受的盐或体内可降解的酯；制备它们的方法、含有它们的制药组合物以及它们在治疗细胞因子介导的疾病或医疗状况中的用途。
• COMPOUNDS HAVING A CYCLIC MOIETY AND COMPOSITIONS FOR DELIVERING ACTIVE AGENTS
  申请人：Tang Pingwah

  公开号：US20100074861A1

  公开（公告）日：2010-03-25

  Compounds comprising cyclic moiety and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.

  本发明提供了由环状基团组成的化合物和用于传递活性剂的组合物。同时也提供了其管理和制备方法。