2-甲基-3-(3-硝基苯基)丙烯酸 | 124525-54-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-甲基-3-(3-硝基苯基)丙烯酸
• 英文名称: m-nitro-α-methylcinnamic acid
• 英文别名: 2-methyl-3-(3-nitrophenyl)propenoic acid；2-Methyl-3-(3-nitro-phenyl)-acrylic acid；(E)-2-methyl-3-(3-nitrophenyl)prop-2-enoic acid
• CAS: 124525-54-8
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: DMXDUJPYGUWROU-FNORWQNLSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  371.5±25.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-3-(3-硝基苯基)丙烯酸 在 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 生成 α-methyl-m-nitrocinnamic acid chloride
  参考文献：
  名称：

  通过 Curtius 重排从 (E)-3-Aryl-2-甲基丙烯酸方便有效地一锅法合成芳基丙酮

  摘要：

  开发了一种方便有效的方法，用于通过 Curtius 重排从 (E)-3-芳基-2-甲基丙烯酸合成芳基丙酮。(E)-3-芳基-2-甲基丙烯酰叠氮化物的Curtius重排和随后的水解在四氯化碳和含有催化量四丁基溴化铵的水的两相介质中在温和的温度下进行，得到82-93中的相应衍生物％ 屈服。

  DOI：

  10.1055/s-0036-1588905
• 作为产物：
  描述：

  间硝基苯胺 在 盐酸 作用下， 生成 2-甲基-3-(3-硝基苯基)丙烯酸
  参考文献：
  名称：

  Testosterone acts as a coronary vasodilator by a calcium antagonistic action

  摘要：

  T acts as a vasodilator in vitro and in vivo. Supplemental T therapy in humans with angina improves symptoms and reduces objective measures of ischemia. In left anterior descending coronary arteries taken from adult male Wistar rats, T abolishes 100 4.2% of calcium-dependent contraction induced by potassium chloride, 82.3+/-6.1% of the mostly calcium-dependent contraction induced by prostagiandin-F-2-alpha, but only 45.3+/-3.4% of the contraction induced by phorbol-1 2,1 3-dibutyrate (PDBu) in the presence of extracellular calcium, and 54.5+/-4.5% of the contraction induced by PDBu in the absence of extracellular calcium. These findings suggest that T is primarily inhibiting the calcium-dependent elements of vascular contraction.

  DOI：

  10.1007/bf03344037

文献信息

• Carboxamide compounds as SRS-A antagonists
  申请人：Pfizer Inc.

  公开号：US04331683A1

  公开（公告）日：1982-05-25

  The compounds of the invention are certain new propenamides and 2-butenamides having a (carboxyalkanamido)phenyl or a (carboxyalkenamido)phenyl group at the 3-position, and certain esters thereof, and certain cyclopropanecarboxamide compounds having a (carboxyalkanamido)phenyl group or a (carboxyalkenamido)phenyl group at the 2-position, and certain esters thereof. The compounds are useful for antagonizing the spasmogenic activity of slow-reacting substance of anaphylaxis (SRS-A) in a human subject. In particular, the compounds of the invention are useful for preventing and treating certain obstructive airways diseases, notably allergic bronchial asthma, allergic rhinitis and certain skin disorders, in human subjects.

  本发明的化合物是具有（羧基烷酰胺基）苯基或（羧基烯酰胺基）苯基基团位于3位的某些新丙烯酰胺和2-丁烯酰胺，以及它们的某些酯，以及具有（羧基烷酰胺基）苯基基团或（羧基烯酰胺基）苯基基团位于2位的某些环丙烷羧酰胺化合物，以及它们的某些酯。这些化合物对于拮抗人体内过敏性反应缓激物（SRS-A）的痉挛原活性是有用的。特别是，本发明的化合物对于预防和治疗某些阻塞性气道疾病，尤其是过敏性支气管哮喘、过敏性鼻炎和某些皮肤疾病在人体中是有用的。
• (Carboxy-oxo-pyrrolidino)phenylalkenamides and esters thereof as SRS-A
  申请人：Pfizer Inc.

  公开号：US04296120A1

  公开（公告）日：1981-10-20

  Certain new propenamide and 2-butenamide compounds, having a (4-carboxy-2-oxo-pyrrolidino)phenyl substituent at the 3-position, and certain esters thereof, and their use for antagonizing the spasmogenic activity of slow-reacting substance of anaphylaxis (SRS-A) in a human subject. In particular, the compounds of the invention are useful for preventing and treating certain obstructive airways diseases, notably allergic bronchial asthma, allergic rhinitis and certain skin disorders, in human subjects.

  某些新的丙烯酰胺和2-丁烯酰胺化合物，在3位具有(4-羧基-2-氧代吡咯啉基)苯基取代基，以及它们的某些酯，以及它们在人体中用于拮抗过敏性反应缓慢反应物质(SRS-A)的痉挛原活性。特别是，本发明的化合物对于预防和治疗某些阻塞性气道疾病，特别是过敏性支气管哮喘、过敏性鼻炎和某些皮肤疾病，在人体中具有用处。
• (Carboxyacylamino)phenylalkenamides and esters thereof as SRS-A
  申请人：Pfizer, Inc.

  公开号：US04296129A1

  公开（公告）日：1981-10-20

  Certain new propenamides and 2-butenamides having a (carboxyalkanamido)phenyl or a (carboxyalkenamido)phenyl group at the 3-position, and certain esters thereof, and their use for antagonizing the spasmogenic activity of slow-reacting substance of anaphylaxis (SRS-A) in a human subject. In particular, the compounds of the invention are useful for preventing and treating certain obstructive airways diseases, notably allergic bronchial asthma, allergic rhinitis and certain skin disorders, in human subjects.

  具有（羧基烷酰胺基）苯基或（羧基烯酰胺基）苯基基团位于3位的某些新型丙烯酰胺和2-丁烯酰胺，以及它们的某些酯，以及它们在人体中用于拮抗过敏性缓慢反应物质（SRS-A）的痉挛原活性的用途。特别是，本发明的化合物对于预防和治疗某些阻塞性气道疾病特别有用，尤其是过敏性支气管哮喘、过敏性鼻炎和某些皮肤疾病，在人体中。
• Synthesis and structure-activity study of protease inhibitors. I. (Guanidinophenyl)propionate and guanidinocinnamate derivatives.
  作者：TOSHIYUKI OKUTOME、HIROYUKI KAWAMURA、SEIZO TAIRA、TOYOO NAKAYAMA、SHIGEKI NUNOMURA、MASATERU KURUMI、YOJIRO SAKURAI、TAKUO AOYAMA、SETSURO FUJII

  DOI：10.1248/cpb.32.1854

  日期：——

  Guanidino-ester derivatives were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin and Cl esterase, as well as on in vitro complement-mediated hemolysis. Among the compounds synthesized, phenyl α-ethyl-p-guanidinocinnamate (IVg) and phenyl α-propyl-p-guanidinocinnamate (IVh) exhibited potent and selective Cl esterase inhibition (IC50 : 7×10-6 and 6×10-6 M, respectively) and 6-methyl-3-pyridyl α-ethyl-p-guanidinocinnamate (IVi) markedly suppressed complement-mediated hemolysis (86% inhibition at 1×10-3M).

  合成了氨基脲酯衍生物，并评估了其对胰蛋白酶、纤溶酶、激肽释放酶、血栓素和补体酯酶的抑制活性，以及在体外补体介导的溶血作用。在合成的化合物中，苯基α-乙基-p-氨基脲肉桂酸酯（IVg）和苯基α-丙基-p-氨基脲肉桂酸酯（IVh）表现出了强效和选择性Cl酯酶抑制（IC50：7×10^-6和6×10^-6 M，分别），而6-甲基-3-吡啶基α-乙基-p-氨基脲肉桂酸酯（IVi）显著抑制了补体介导的溶血（1×10^-3M下抑制率为86%）。
• Amino- or guanidino-phenylpropionic acid derivatives
  申请人：Torii & Co., Ltd.

  公开号：US04182897A1

  公开（公告）日：1980-01-08

  Amino- or guanidino-phenylpropionic ester derivatives represented by the formula: ##STR1## wherein R is --NH.sub.2 or ##STR2## R.sup.1 is hydrogen or a lower alkyl group, and R.sup.2 is an unsubstituted or a lower-alkyl-, carboxyalkyl-, lower-alkoxy-, lower-alkoxycarbonyl- or halogen-substituted phenyl group or an unsubstituted or a halogen-substituted naphthyl group, and acid addition salts thereof are novel compounds exhibiting a specific enzyme-inhibitory activity to proteolytic enzymes and, therefore, they are useful as the therapeutic agent of diseases induced by abnormal activation of these enzymes. The above-mentioned compounds can be produced by subjecting a nitrocinnamic acid derivative represented by the formula: ##STR3## and a phenol derivative or a naphthol derivative represented by the formula: HO--R.sup.2 to an esterification in the conventional manner to obtain a nitrocinnamic ester derivative, then reducing the latter compound to obtain an aminophenylpropionic ester derivative and, if desired, reacting it with cyanamide to obtain a guanidino-phenylpropionic ester derivative and, if desired, further converting the reaction product to an acid addition salt.

  Amino-或guanidino-苯丙酸酯衍生物的化学式表示为：其中R为--NH.sub.2或R.sup.1为氢或较低的烷基基团，R.sup.2为未取代或较低烷基，羧基烷基，较低烷氧基，较低烷氧羰基或卤素取代的苯基或未取代或卤素取代的萘基，以及它们的酸盐是一种新颖的化合物，具有特定的对蛋白酶酶抑制活性，因此它们可用作治疗由这些酶异常激活引起的疾病的治疗剂。上述化合物可通过将化学式表示为的硝基肉桂酸衍生物和酚衍生物或萘酚衍生物进行酯化反应以获得硝基肉桂酸酯衍生物，然后还原后者化合物以获得氨基苯丙酸酯衍生物，并且如果需要，与氰胺反应以获得鸟氨基苯丙酸酯衍生物，并且如果需要，进一步将反应产物转化为酸盐。