methyl (3-pentylphenyl)acetate | 1002101-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (3-pentylphenyl)acetate
• 英文别名: methyl 2-[3-pentylphenyl]acetate；Methyl 2-(3-pentylphenyl)acetate
• CAS: 1002101-12-3
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XUQJUGORGAHUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (3-pentylphenyl)acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以100%的产率得到2-(3-pentylphenyl)acetic acid
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q
• 作为产物：
  描述：

  methyl [3-(1-pentynyl)phenyl]acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以99%的产率得到methyl (3-pentylphenyl)acetate
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q

文献信息

• [EN] SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL USES THEREOF<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET UTILISATIONS PHARMACEUTIQUES DE CEUX-CI
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2010127440A1

  公开（公告）日：2010-11-11

  The present invention relates to substituted aromatic compounds of Formula (I) and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds in the prevention and/or treatment of various diseases and conditions in subjects, including the prevention or treatment of (i) blood disorders, (ii) renal disorders, nephropathies, or renal disorder complications; (iii) inflammatory-related diseases; and/or (iv) oxidative stress related disorders.

  本发明涉及式(I)的取代芳香化合物及其医药用途。发明的特定方面涉及在受试者中预防或治疗各种疾病和状况的用途，包括预防或治疗(i)血液病(ii)肾脏疾病、肾病或肾脏疾病并发症；(iii)炎症相关疾病；和/或(iv)氧化应激相关紊乱。
• [EN] SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR TISSUE SELF-REPAIR AND REGENERATION<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET COMPOSITIONS PHARMACEUTIQUES POUR AUTO-RÉPARATION ET RÉGÉNÉRATION DE TISSU
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2016074068A1

  公开（公告）日：2016-05-19

  Described herein are compounds of Formula I, or pharmaceutically acceptable salts thereof, or combinations thereof, as well as uses thereof. Such uses include promoting tissue self-repair or tissue regeneration of an organ, stimulating the generation of tissue growth, modulating (e.g. increasing) the level of a tissue-repair marker, treating physical injury in an organ, tissue, or cell, promoting wound healing as well as anti-aging applications. Corresponding compositions, methods and uses are also described. Formula I wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F of OH; R2 is H, F, OH, C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH, or CH2Ph; R4 is H, F or OH; Q is 1) (CH2),C(0)OH wherein m is 1 or 2 2) CH(CH3)C(0)OH, 3) C(CH3)2C(0)OH, 4) CH(F)-C(0)OH, 5) CF2-C(0)OH or 6) C(0)-C(0)OH.

  以下是公式I的化合物，或其药用可接受的盐，或它们的组合，以及它们的用途。这些用途包括促进器官的组织自我修复或组织再生，刺激组织生长的生成，调节（例如增加）组织修复标志物的水平，治疗器官、组织或细胞的物理损伤，促进伤口愈合以及抗衰老应用。还描述了相应的组合物、方法和用途。公式I中，A是C5烷基，C6烷基，C5烯基，C6烯基，C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R1是H，F或OH；R2是H，F，OH，C5烷基，C6烷基，C5烯基，C6烯基，C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R3是H，F，OH或CH2Ph；R4是H，F或OH；Q是1）（CH2）mC(0)OH，其中m为1或2 2）CH(CH3)C(0)OH，3）C(CH3)2C(0)OH，4）CH(F)-C(0)OH，5）CF2-C(0)OH或6）C(0)-C(0)OH。
• [EN] SUBSTITUTED AROMATIC COMPOUNDS FOR THE TREATMENT OF PULMONARY FIBROSIS, LIVER FIBROSIS, SKIN FIBROSIS AND CARDIAC FIBROSIS<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS POUR TRAITEMENT DE LA FIBROSE PULMONAIRE, DE LA FIBROSE HÉPATIQUE, DE LA FIBROSE CUTANÉE ET DE FIBROSE CARDIAQUE
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2014138907A1

  公开（公告）日：2014-09-18

  The present invention relates to substituted aromatic compounds for use in prevention or treatment of various fibrotic diseases and conditions in subjects, including pulmonary fibrosis, liver fibrosis, skin fibrosis and cardiac fibrosis, where the compound has the following formula: or a pharmaceutically acceptable salt thereof, wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, OH or F; R2 is H, OH, F or CH2-OH; R3 is H, OH, F or CH2Ph; R4 is H, OH or F; Q is 1 ) (CH2)mC(O)OH wherein m is 1 or 2, 2) CH(CH3)C(O)OH, 3) C(CH3)2C(O)OH, 4) CH(F)-C(O)OH, 5) CF2-C(O)OH, or 6) C(O)-C(O)OH.

  本发明涉及用于预防或治疗主体中的各种纤维化疾病和状况，包括肺纤维化、肝纤维化、皮肤纤维化和心脏纤维化的取代芳香族化合物，其中化合物具有以下公式：或其药学上可接受的盐，其中A为C5烷基，C6烷基，C5烯基，C6烯基，C（O）-（CH2）n-CH3或CH（OH）-（CH2）n-CH3，其中n为3或4；R1为H，OH或F；R2为H，OH，F或CH2-OH；R3为H，OH，F或CH2Ph；R4为H，OH或F；Q为1）（CH2）mC（O）OH，其中m为1或2，2）CH（CH3）C（O）OH，3）C（CH3）2C（O）OH，4）CH（F）-C（O）OH，5）CF2-C（O）OH或6）C（O）-C（O）OH。
• Substituted Aromatic Compounds and Pharmaceutical Uses thereof
  申请人：Zacharie Boulos

  公开号：US20120088784A1

  公开（公告）日：2012-04-12

  The present invention relates to substituted aromatic compounds of Formula I and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds in the prevention and/or treatment of various diseases and conditions in subjects, including the prevention or treatment of (i) blood disorders, (ii) renal disorders, a nephropathies, or renal disorder complications; (iii) inflammatory-related diseases; and/or (iv) oxidative stress related disorders.

  本发明涉及式I的取代芳香化合物及其药物用途。本发明的特定方面涉及使用这些化合物预防和/或治疗受试者的各种疾病和病况，包括预防或治疗(i)血液疾病，(ii)肾脏疾病、肾病或肾脏疾病并发症；(iii)炎症相关疾病；和/或(iv)氧化应激相关疾病。
• Salts of 3-Pentylphenylacetic Acid and Pharmaceutical Uses Thereof
  申请人：Zacharie Boulos

  公开号：US20120095102A1

  公开（公告）日：2012-04-19

  The present invention relates to salts of 3-pentylphenylacetic acid and their pharmaceutical uses. Particular aspects of the invention relate to the use of those salts in the prevention and/or treatment of various diseases and conditions in subjects, including the prevention and treatment of (i) blood disorders, (ii) renal disorders and renal disorder complications; (iii) inflammatory-related diseases; and/or (iv) oxidative stress related disorders.

  本发明涉及3-戊基苯乙酸盐及其药物用途。本发明的特定方面涉及在受试者中预防和/或治疗各种疾病和病症中使用这些盐，包括预防和治疗（i）血液疾病，（ii）肾脏疾病和肾脏疾病并发症；（iii）与炎症有关的疾病；和/或（iv）与氧化应激有关的疾病。