N-cinnamoylproline | 76084-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cinnamoylproline
• 英文别名: N-cinnamoyl-L-proline；1-(3-Phenylacryloyl)-L-proline；(2S)-1-(3-phenylprop-2-enoyl)pyrrolidine-2-carboxylic acid
• CAS: 76084-32-7
• 化学式: C₁₄H₁₅NO₃
• mdl: MFCD16377067
• 分子量: 245.278
• InChiKey: WSBOYOYQOJYXMU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[(E)-cinnamoylamino]-pyrrolidine-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 N-cinnamoylproline
  参考文献：
  名称：

  4H-3,1-benzoxazin-4-one derivative

  摘要：

  以下是公式（I）所代表的4H-3,1-苯并噁嗪-4-酮衍生物的中文翻译：其中R.sup.1代表较低的烷基，R.sup.2代表较低的烷基，较低的烷硫烷基，或较低的烷基磺酰基，R.sup.3代表氢原子，羟基，较低的烷氧基，或较低的酰氧基，X代表从丙氨酸，缬氨酸和苯丙氨酸组成的氨基酸残基，n代表0、1或2的整数，Y表示从具有2至6个碳原子的烷酰基中选择的取代基，该基可能被苯基取代，苄氧羰基，较低的烷氧羰基，肉桂酰基和甲氧基琥珀酰基。这些衍生物表现出强烈的丝氨酸蛋白酶抑制作用，并可用作预防和治疗由丝氨酸蛋白酶过度作用引起的疾病的有效成分，例如肺炎，肺气肿，纤维肺，支气管炎，关节炎，胰腺炎，肾炎，休克，败血症和动脉硬化。

  公开号：

  US05204462A1

文献信息

• 4H-3,1-benzoxazin-4-one derivative
  申请人：Japan Tobacco, Inc.

  公开号：US05204462A1

  公开（公告）日：1993-04-20

  4H-3,1-benzoxazin-4-one derivatives represented by formula (I) below: ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a lower alkyl group, a lower alkylthioalkyl group, or a lower alkanesulfinylalkyl group, R.sup.3 represents a hydrogen atom a hydroxyl group, a lower alkoxy group, or a lower acyloxy group, X represents an amino acid residue selected from the group consisting of alanine, valine, and phenylalanine, n represents an integer of 0, 1, or 2, and Y means a substituent selected from the group consisting of an alkanoyl group having 2 to 6 carbon atoms which may be substituted by a phenyl group, a benzyloxycarbonyl group, a lower alkoxycarbonyl group, a cinnamoyl group, and a methoxysuccinyl group. These derivatives exhibit a strong serine protease inhibiting effect, and are useful as effective components of agents for preventing and curing diseases caused by the excessive effect of serine proteases, e.g., pneumonia, pulmonary emphysema, fibroid lung, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, and arteriosclerosis.

  以下是公式（I）所代表的4H-3,1-苯并噁嗪-4-酮衍生物的中文翻译：其中R.sup.1代表较低的烷基，R.sup.2代表较低的烷基，较低的烷硫烷基，或较低的烷基磺酰基，R.sup.3代表氢原子，羟基，较低的烷氧基，或较低的酰氧基，X代表从丙氨酸，缬氨酸和苯丙氨酸组成的氨基酸残基，n代表0、1或2的整数，Y表示从具有2至6个碳原子的烷酰基中选择的取代基，该基可能被苯基取代，苄氧羰基，较低的烷氧羰基，肉桂酰基和甲氧基琥珀酰基。这些衍生物表现出强烈的丝氨酸蛋白酶抑制作用，并可用作预防和治疗由丝氨酸蛋白酶过度作用引起的疾病的有效成分，例如肺炎，肺气肿，纤维肺，支气管炎，关节炎，胰腺炎，肾炎，休克，败血症和动脉硬化。
• Nitrile derivatives that inhibit cathepsin K
  申请人：——

  公开号：US20010008901A1

  公开（公告）日：2001-07-19

  Compounds of the formula: 1 wherein R 1 to R 7 and Y are as defined in the specification, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof, are useful for treating diseases associated with cystein proteases, such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  该公式化合物：其中R1到R7和Y如规范中定义，并且其药用盐和/或药用酯是用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿性关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血性发作、瞬间性视网膜动脉阻塞、外周动脉闭塞性疾病、血管成形术和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病的有用化合物。
• Method for the preparation of escitalopram
  申请人：Ahmadian Haleh

  公开号：US20050154051A1

  公开（公告）日：2005-07-14

  The invention relates to a method for the preparation of escitalopram by cyanation of optically active intermediates of the formulas (III) and (II) below, and the preparation of such intermediates by optical resolution.

  本发明涉及一种通过对下列光学活性中间体（III）和（II）进行腈化反应制备艾司西酞普兰的方法，以及通过光学分辨法制备此类中间体的方法。
• [EN] METHOD FOR THE PREPARATION OF ESCITALOPRAM<br/>[FR] PROCEDE DE PREPARATION D'ESCITALOPRAM
  申请人：LUNDBECK & CO AS H

  公开号：WO2003051861A1

  公开（公告）日：2003-06-26

  The invention relates to a method for the preparation of escitalopram by cyanation of optically active intermediates of the formulas (III) and (II) below, and the preparation of such intermediates by optical resolution.

  该发明涉及一种通过对式（III）和（II）的光学活性中间体进行氰化反应制备艾司西酞普兰的方法，并通过光学分辨法制备此类中间体的方法。
• NOVEL 4H-3,1-BENZOXAZIN-4-ONE DERIVATIVE
  申请人：Japan Tobacco Inc.

  公开号：EP0480044A1

  公开（公告）日：1992-04-15

  A 4H-3,1-benzoxazin-4-one derivative of general formula (I), which has a potent serine protease inhibitory action and is useful as the active ingredient of drugs for preventing and treating pneumonia, pulmonary emphysema, pulmonary fibrosis, bronchitis, arthritis, pancreatitis, nephritis, shock, sepsis, arteriosclerosis, etc.; wherein R¹ represents lower alkyl; R² represents lower alkyl, lower alkylthioalkyl or lower alkanesulfinylalkyl; R³ represents hydrogen, hydroxyl, lower alkoxy or lower acyloxy; X represents a residue of an amino acid selected from the group consisting of alanine, valine and phenyl-alanine; n is an integer of 0, 1 or 2; and Y represents a substituent selected from the group consisting of C₂ to C₆ alkanoyl optionally substituted with phenyl, benzyloxycarbonyl, lower alkoxycarbonyl, cinnamoyl and methoxysuccinoyl.

  一种通式(I)的4H-3,1-苯并恶嗪-4-酮衍生物，它具有强效的丝氨酸蛋白酶抑制作用，可作为预防和治疗肺炎、肺气肿、肺纤维化、支气管炎、关节炎、胰腺炎、肾炎、休克、败血症、动脉硬化等药物的活性成分。其中 R¹ 代表低级烷基；R² 代表低级烷基、低级烷硫基烷基或低级烷磺基烷基；R³ 代表氢、羟基、低级烷氧基或低级酰氧基；X 代表选自丙氨酸、缬氨酸和苯丙氨酸的氨基酸残基；n 是 0、1 或 2 的整数；以及 Y 代表选自由苯基、苄氧羰基、低级烷氧羰基、肉桂酰基和甲氧基琥珀酰基取代的 C₂ 至 C₆ 烷酰基组成的取代基。