3-(4-(phenoxymethyl)phenyl)propanoic acid | 64264-21-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-(phenoxymethyl)phenyl)propanoic acid
• 英文别名: 3-(4-phenoxymethyl)-phenyl-propionic acid；3-(4-Phenoxymethyl)-phenyl-propionsaeure；3-(p-Phenoxymethyl-phenyl)-propionsaeure；OSe12；3-[4-(phenoxymethyl)phenyl]propanoic acid
• CAS: 64264-21-7
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: DAKROGDTSDTCAY-UHFFFAOYSA-N

物化性质

• 沸点：
  426.3±25.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-(4-(phenoxymethyl)phenyl)propanoic acid 在 草酰氯 作用下， 生成
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r
• 作为产物：
  描述：

  4-碘苄醇 在 NiCl₂(H₂O)6 吡啶 、 sodium hydroxide 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 104.33h， 生成 3-(4-(phenoxymethyl)phenyl)propanoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r

文献信息

• [EN] CARBOXAMIDES DERIVATIVES<br/>[FR] DERIVES DE CARBOXAMIDES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2003106403A1

  公开（公告）日：2003-12-24

  The present invention relates to carboxamides which are useful as an active ingredient of pharmaceutical preparations. The carboxamides of the present invention have IP receptor antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with IP receptor antagonistic activity.Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity.The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension;hemophilia and hemorrhage; and inflammation, since the diseases are alleviated by treatment with an IP receptor antagonist.

  本发明涉及作为药物制剂活性成分有用的羧酰胺。本发明的羧酰胺具有IP受体拮抗活性，可用于预防和治疗与IP受体拮抗活性相关的疾病。这些疾病包括泌尿系统疾病或障碍，如：膀胱出口梗阻、膀胱过度活跃、尿失禁、膀胱逼尿肌过度反射、膀胱逼尿肌不稳定、膀胱容量减少、排尿频率、迫切性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺肥大（BPH）、前列腺炎、尿频、夜尿频、尿急、盆腔过敏、尿道炎、盆腔疼痛综合征、前列腺疼痛综合征、膀胱炎或特发性膀胱过敏。本发明的化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病性疼痛、急性疼痛、慢性疼痛、牙痛、经前疼痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为通过IP受体拮抗剂治疗可以缓解这些疾病。
• Carboxamides derivatives
  申请人：Shimazaki Makoto

  公开号：US20060135613A1

  公开（公告）日：2006-06-22

  The present invention relates to carboxamides which are useful as an active ingredient of pharmaceutical preparations. The carboxamides of the present invention have IP receptor antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with IP receptor antagonistic activity. Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity. The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension; hemophilia and hemorrhage; and inflammation, since the diseases are alleviated by treatment with an IP receptor antagonist.

  本发明涉及一种作为制药制剂活性成分有用的羧酰胺。本发明的羧酰胺具有IP受体拮抗活性，可用于预防和治疗与IP受体拮抗活性相关的疾病。这些疾病包括以下泌尿系统疾病或疾病：膀胱出口梗阻、过度活动的膀胱、尿失禁、膀胱平滑肌过度反射、膀胱平滑肌不稳定、膀胱容量降低、排尿频率、强迫性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺增生症（BPH）、前列腺炎、尿频、夜尿、尿急、盆腔敏感性、尿道炎、盆腔疼痛综合征、前列腺痛、膀胱炎或特发性膀胱敏感性。本发明化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病理性疼痛、急性疼痛、慢性疼痛、牙痛、经前痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为这些疾病通过使用IP受体拮抗剂治疗得到缓解。
• TETRACYCLIC INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Boger Dale L.

  公开号：US20100249078A1

  公开（公告）日：2010-09-30

  Certain tetracyclic compounds are described, which may be used in pharmaceutical compositions and methods for treating disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity. Thus, the compounds may be administered to treat, e.g., anxiety, pain, inflammation, sleep disorders, eating disorders, or movement disorders (such as multiple sclerosis).

  本文描述了某些四环化合物，可用于制备药物组合物和方法，用于治疗由脂肪酸酰胺水解酶（FAAH）活性介导的疾病状态、障碍和病况。因此，这些化合物可以用于治疗焦虑、疼痛、炎症、睡眠障碍、进食障碍或运动障碍（例如多发性硬化）。
• Tetracyclic inhibitors of fatty acid amide hydrolase
  申请人：Boger Dale L.

  公开号：US08372823B2

  公开（公告）日：2013-02-12

  Certain tetracyclic compounds are described, which may be used in pharmaceutical compositions and methods for treating disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity. Thus, the compounds may be administered to treat, e.g., anxiety, pain, inflammation, sleep disorders, eating disorders, or movement disorders (such as multiple sclerosis).

  本文描述了某些四环类化合物，可用于制备药物组合物和治疗由脂肪酸酰胺酶（FAAH）活性介导的疾病状态、疾病和病症的方法。因此，该化合物可用于治疗焦虑、疼痛、炎症、睡眠障碍、饮食障碍或运动障碍（如多发性硬化）等疾病。
• WO2008/147553
  申请人：——

  公开号：——

  公开（公告）日：——