2-propoxyethyl 3-aminobut-2-enoate | 43107-09-1

• 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: 2-propoxyethyl 3-aminobut-2-enoate
• 英文别名: 2-(n-propoxy)ethyl 3-aminocrotonate
• CAS: 43107-09-1
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: PBJZBRWKTBIWOK-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.7 Torr)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diisopropyl 1-(3-nitrobenzylidene)-acetonylphosphonate 、 2-propoxyethyl 3-aminobut-2-enoate 以 异丙醇 为溶剂， 以72%的产率得到2-n-propoxyethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-diisopropoxyphosphinyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Antihypertensive phosphono derivatives of hantzsch dihydropyridines

  摘要：

  式(I)中的二氢吡啶衍生物及其药学上可接受的盐，其中R1-R7如定义，制备这些化合物的方法以及用于治疗心脏病、循环障碍和高血压的这些化合物的药物组合物和方法。

  公开号：

  US04535073A1
• 作为产物：
  描述：

  acetoacetic acid β-propoxyethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-propoxyethyl 3-aminobut-2-enoate
  参考文献：
  名称：

  Synthesis of new water-soluble dihydropyridine vasodilators.

  摘要：

  制备了几种水溶性二氢吡啶血管扩张剂，并评估了它们的血管扩张活性。其中，2-（N-苯基-N-甲基氨基）-乙基-甲基-2, 6-二甲基-4-（m-硝基苯基）-1, 4-二氢吡啶-3, 5-二羧酸盐盐酸盐（YC-93）被发现具有出色的活性和生物利用度。对该化合物的各种合成路线进行了研究。

  DOI：

  10.1248/cpb.27.1426

文献信息

• An efficient synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines and application in cyclisation reactions
  作者：Brigita Vigante、Aiva Plotniece、Martins Rucins、Marina Petrova、Ruslan Muhamadejev、Karlis Pajuste、Sergey Belyakov、Yuriy G. Shermolovich、Arkadij Sobolev

  DOI：10.1016/j.tet.2018.03.075

  日期：2018.5

  synthetic usefulness of obtained 4-nitrobuta-1,3-dien-1-amines has also been demonstrated by achieving the synthesis of multisubstituted 5-nitro-1,6-dihydropyridines in two-component cyclocondensation reactions of 4-nitrobuta-1,3-dien-1-amines with aromatic or aliphatic aldehydes. Lastly, diverse N-H and N-substituted 5-nitro-1,6-dihydropyridines have been obtained in 35–87% yields.

  由3-氨基巴豆酸酯和硝基乙醛钾盐合成多取代的4-nitrobuta-1,3-dien-1-amines（nitrodienamines）的产率为45-89％。这一一步方案可与各种NH和N-取代的3-氨基巴豆酸酯有效结合，并同时提供伯氮和仲氮二烯胺。另外，已经显示了4-硝基丁-1，3-二烯-1-胺的2和3位上的取代基的可能变化。通常，仲4-硝基丁-1,3-dien-1-胺的收率低于伯。通过在4-硝基丁-1的两组分环缩合反应中实现多取代的5-硝基-1,6-二氢吡啶的合成，也证明了所获得的4-硝基buta-1,3-dien-1-胺的合成有用性。 3-dien-1-胺与芳族或脂族醛。
• Novel oxadiazolyl-1,4-dihydropyridines useful as antihypertensive agents
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US04705786A1

  公开（公告）日：1987-11-10

  A compound of the formula ##STR1## wherein T.sub.1 is lower alkylene, lower alkenylene or a single bond; X is ##STR2## T.sub.2 is carbonyl, lower alkylene or a single bond; R.sub.2 is phenyl, phenoxy, pyridyl, pyrimidinyl, furyl, thienyl, lower cycloalkyl or adamantyl; R.sub.2 and R.sub.6, when taken together with the nitrogen to which they are attached form pyrrolidinyl, piperidinyl or azacyclooctanyl; R.sub.14 is COOR.sub.8 or --R.sub.3 R.sub.9 wherein T.sub.3 is lower alkylene and R.sub.9 is lower alkoxy, lower cycloalkyl, cyano, polyfluoro-lower alkyl or pyridyl; and R.sub.1 and R.sub.5 are each lower alkyl or lower alkenyl, useful in the treatment of cardiovascular diseases.

  一种化合物，其化学式为##STR1##其中T.sub.1为较低的烷基，较低的烯基或单键；X为##STR2##T.sub.2为羰基，较低的烷基或单键；R.sub.2为苯基，苯氧基，吡啶基，嘧啶基，呋喃基，噻吩基，较低的环烷基或戊二烯基；当R.sub.2和R.sub.6与它们连接的氮一起形成吡咯啉基，哌啶基或氮杂环辛基时，R.sub.2和R.sub.6；R.sub.14为COOR.sub.8或--R.sub.3 R.sub.9，其中T.sub.3为较低的烷基，R.sub.9为较低的烷氧基，较低的环烷基，氰基，多氟较低烷基或吡啶基；R.sub.1和R.sub.5分别为较低的烷基或较低的烯基，用于治疗心血管疾病。
• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. I.
  作者：IWAO MORITA、SHIN-ICHI TADA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.3898

  日期：——

  A series of phosphonate derivatives, designed as analogues of 1, 4-dihydropyridine-3, 5- dicarboxylates in which a phosphonate group was introduced instead of the carboxylate group at the 5-position, was synthesized, and their antihypertensive activities were examined. Among the compounds examined, 5-diallyloxyphosphinyl-1, 4-dihydropyridine-3-carboxylates were most effective in lowering the blood pressure in normotensive rats and spontaneously hypertensive rats (SHR). The phosphonate derivatives are considered to be close analogues of the carboxylate derivatives. The structure-activity relationships are discussed.

  一系列膦酸盐衍生物被设计为1,4-二氢吡啶-3,5-二羧酸盐的类似物，其中在5-位引入了膦酸基团而非羧酸基团，这些化合物被合成并检测了它们的降血压活性。在所研究的化合物中，5-二烯丙氧基膦基-1,4-二氢吡啶-3-羧酸盐在降低正常血压大鼠和自发性高血压大鼠（SHR）的血压方面最为有效。这些膦酸盐衍生物被认为是羧酸盐衍生物的近似类似物。结构-活性关系在此进行了讨论。
• Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.
  作者：IWAO MORITA、KATSUTOSHI KUNIMOTO、MASAMI TSUDA、SHIN-ICHI TADA、MASAHIRO KISE、KIYOSHI KIMURA

  DOI：10.1248/cpb.35.4144

  日期：——

  A series of 1, 4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1, 4- dihydropyridine-3, 5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2, 6-dimethyl-5- (2-oxo-1, 3, 2-dioxaphosphorinan-2-yl) -4- (2-nitrophenyl) -1, 4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。
• Calcium Level Controlling Activities of Novel Derivatives of Amlodipine,Riodipine and Cerebrocrast
  作者：R. Vilskersts、B. Vigante、Z. Neidere、A. Krauze、I. Domracheva、L. Bekere、I. Shestakova、G. Duburs、M. Dambrova

  DOI：10.2174/157018012799129909

  日期：2012.3.1

  A novel series of asymmetric 4-aryl-1,4-dihydropyridine (1,4-DHP) 3,5-diester derivatives and their symmetric analogues comprised of functional moieties of amlodipine, riodipine and cerebrocrast have been synthesized. The calcium channel blocking activity was evaluated in an isolated rat aortic ring model. The calcium overload preventing activity was tested in SH-SY5Y neuroblastoma cell line by a fluorescence-based calcium assay. Among synthesized and tested compounds, 4a showed the highest calcium overload preventing activity (IC50=39μM) and 7e demonstrated the highest calcium channel inhibiting activity (EC50=0.2 nM). Asymmetric ester 7a exerted both substantial calcium channel blocking and calcium overload preventing activity.

  一种新型的不对称4-芳基-1,4-二氢吡啶（1,4-DHP）3,5-二酯衍生物及其对称类似物，包含了氨氯地平、利多卡因和脑坏死素的功能基团，已被合成。钙通道阻断活性在孤立的大鼠主动脉环模型中进行了评估。钙过载预防活性通过基于荧光的钙测定在SH-SY5Y神经母细胞瘤细胞系中进行了测试。在合成并测试的化合物中，4a表现出最高的钙过载预防活性（IC50=39μM），而7e显示出最高的钙通道抑制活性（EC50=0.2 nM）。不对称酯7a则同时展现了显著的钙通道阻断和钙过载预防活性。