(E)-3-Amino-but-2-enoic acid 2-methoxy-ethyl ester | 143093-34-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-Amino-but-2-enoic acid 2-methoxy-ethyl ester
• 英文别名: 2-Methoxyethyl 3-aminobut-2-enoate；2-methoxyethyl (E)-3-aminobut-2-enoate
• CAS: 143093-34-9
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: XJOLYWNYMOPRKQ-AATRIKPKSA-N

物化性质

• 沸点：
  259.4±15.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-Amino-but-2-enoic acid 2-methoxy-ethyl ester 、 2-[1-(3-Nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid 2-(1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-ethyl ester 以 乙醇 为溶剂， 反应 10.0h， 以51%的产率得到2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-methoxy-ethyl) ester 5-[2-(1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethyl] ester
  参考文献：
  名称：

  Synthesis of 3-[(2,3-dihydro-1,1,3-trioxo-1,2-benzisothiazol-2-yl)alkyl] 1,4-dihydropyridine-3,5-dicarboxylate derivatives as calcium channel modulators

  摘要：

  1,4-Dihydropyridine (DHP) derivatives with a 1,2-benzisothiazol-3-one 1,1-dioxide group, linked through an alkylene bridge to the C-3 carboxylate of the DHP ring, with both vasconstricting and vasorelaxant properties were obtained. In blocking Ca2+-evoked contractions of K+-depolarized rabbit aortic strips, compounds 12 and 41 were 10-fold more potent than nifedipine; 27 other compounds were 1-4-fold more potent. Their vascular versus cardiac selectivity was very pronounced; for instance, the selectivity index for compound 41 was 70-fold higher than that of nifedipine. This was also true for the vasoconstricting compound 22, which was as potent as Bay K 8644 in enhancing the Ca2+-evoked contractions of rabbit aorta strips, yet it had poor inotropic activity in rabbit left atria. Oral adminstration of compounds 38, 40, 43, and 53 (20 mg/kg) caused a 35-37% decrease in systolic blood pressure in spontaneously hypertensive rats (SHR); these effects were similar to those of nifedipine. However, iv administration of these compounds to anesthetized SHR caused a decrease in blood pressure which was more pronounced and long-lasting than that of nifedipine. When administered iv at 100-mu-g/kg, the vasoconstricting compound 22 caused a 40% increase in systolic and diastolic blood pressure. Compound 22 exhibited an unusually interesting feature over the other five Ca2+ DHP agonists: it had diester substitutions at the C-3 and C-5 positions of the DHP ring. Overall, compounds processing these properties might be useful in treating clinical cardiovascular conditions in which DHP Ca2+ antagonists or agonists are indicated.

  DOI：

  10.1021/jm00091a008
• 作为产物：
  描述：

  乙酰乙酸甲氧乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 (E)-3-Amino-but-2-enoic acid 2-methoxy-ethyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of Pyrrolo[3,4-b]pyridines and Related Pyridine-Fused Heterocycles

  摘要：

  DOI：

  10.1055/s-1999-3618

文献信息

• 4-Alkyl-1,4-dihydropyridine derivatives as specific PAF-acether antagonists
  作者：Carlos E. Sunkel、Miguel Fau de Casa-Juana、Luis Santos、M. Mar Gomez、Mercedes Villarroya、M. Antonia Gonzalez-Morales、Jaime G. Priego、M. Pilar Ortega

  DOI：10.1021/jm00174a017

  日期：1990.12

  A new series of 4-alkyl-1,4-dihydropyridines (1,4-DHP) were synthesized and evaluated for their ability to inhibit washed rabbit platelet aggregation induced by PAF-acether (1-O-hexadecyl/octadecyl-2-O-acetyl-sn-glycero-3-phosphorylcholine) and to reverse PAF-induced hypotension in anesthetized rats. Additionally, compounds were evaluated for their ability to inhibit the binding of radiolabeled PAF to its receptor on rabbit platelets. Among these compounds, 6I and 6L were the most potent and specific antagonists. At concentrations up to 100 microM, neither compound 6I nor compound 6L caused platelet aggregation nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Compound 6L did not show in vitro calcium channel blocker activity measured on vascular smooth muscle preparations of rabbit aorta and on [3H]nitrendipine binding assays. The compound did not show any cardiovascular effects in anesthetized rat at iv doses up to 1000 micrograms/kg, and the Ki value was 568.62 nmol. These results indicate that compound 6L is a potent and specific PAF antagonist with 1,4-dihydropyridine structure but devoid of a significant cardiovascular activity related to calcium-antagonist properties.
• Dubur; Veveris; Weinheimer, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 10, p. 1185 - 1189
  作者：Dubur、Veveris、Weinheimer、Bisenieks、Makarova、Kimenis、Uldrikis、Lukevics、Dooley、Osswald

  DOI：——

  日期：——
• CHO, HIDETSURA;UEDA, MASARU;MIZUNO, AKIRA;ISHIHARA, TAKAFUMI;AISAKA, KAZU+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2117-2121
  作者：CHO, HIDETSURA、UEDA, MASARU、MIZUNO, AKIRA、ISHIHARA, TAKAFUMI、AISAKA, KAZU+

  DOI：——

  日期：——
• SUNKEL, CARLOS E.;DE, CASA-JUANA MIGUEL FAU;SANTOS, LUIS;GOMEZ, M. MAR;VI+, J. MED. CHEM., 33,(1990) N2, C. 3205-3210
  作者：SUNKEL, CARLOS E.、DE, CASA-JUANA MIGUEL FAU、SANTOS, LUIS、GOMEZ, M. MAR、VI+

  DOI：——

  日期：——
• MEYER H.; BOSSERT F.; WEHINGER E.; STOEPEL K.; VATER W., ARZNEIMITTEL-FORSCH., 1981, 31, NO 3, 407-409
  作者：MEYER H.、 BOSSERT F.、 WEHINGER E.、 STOEPEL K.、 VATER W.

  DOI：——

  日期：——