3,3-二氨基丙烯腈 | 266338-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,3-二氨基丙烯腈
• 英文名称: 3,3-Diaminoacrylnitril
• 英文别名: 3,3-diaminoacrylonitrile；3,3-diaminoprop-2-enenitrile
• CAS: 266338-29-8
• 化学式: C₃H₅N₃
• mdl: MFCD09955287
• 分子量: 83.0928
• InChiKey: DQDDGCDRIVTXOX-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 沸点：
  416.1±30.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丁酸,2-[(4-甲氧苯基)亚甲基]-3-羰基-,乙基酯 、 3,3-二氨基丙烯腈 以 甲醇 为溶剂， 反应 0.25h， 以987 mg的产率得到ethyl 6-amino-5-cyano-2-methyl-4-(4-methoxyphenyl)-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease

  摘要：

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.

  DOI：

  10.1021/jm801292b
• 作为产物：
  描述：

  2-氰基乙脒酸乙酯盐酸盐 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 3,3-二氨基丙烯腈
  参考文献：
  名称：

  Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease

  摘要：

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.

  DOI：

  10.1021/jm801292b

文献信息

• Synthese von substituierten 2-Aminonicotinonitrilen
  作者：Reinhard Troschütz、Thomas Dennstedt

  DOI：10.1002/ardp.19943270107

  日期：——

  Mono‐, di‐ und trisubstituierte 2‐Aminonicotinonitrile vom Typ 8, 13, 14 und 19 lassen sich aus Keton‐Mannich‐Basen Hydrochloriden 4 · HCl, Enonen 12, β‐Aminovinylketonen 17, 3‐Aminoacrolein‐Derivaten 18 sowie Vinamidinium Perchloraten 21 und in situ erzeugtem 3,3‐Diamino‐acrylnitril (3) herstellen.

  可以从酮曼尼希碱、盐酸盐 4 HCl、烯酮 12、β-氨基乙烯基酮 17、3-氨基丙烯醛衍生物 18 和 vinamidinium 和高氯酸盐中获得 8、13、14 和 19 型的单、二和三取代的 2-氨基烟腈3,3-二氨基-丙烯腈 (3) 原位生成。
• Synthesis of 3-EWG-Substituted 2-Amino-5-hydroxyindoles via Nenitzescu Reaction
  作者：Reinhard Troschütz、Jens Landwehr

  DOI：10.1055/s-2005-872074

  日期：——

  A series of primary ketene aminals 2, substituted with an electron-withdrawing group were reacted with 1,4-benzoquinone (1) yielding new 3-EWG-substituted 2-amino-5-hydroxyindoles 3a-f. Treatment of ethyl 3,3-diaminoacrylate (2a) with naphthoquinone (20a) and heteroaromatic quinones 20b-d afforded [g]annulated 2-aminoindole-3-carboxylates 21a-d.

  一系列被吸电子基团取代的伯烯酮缩醛胺 2 与 1,4-苯醌 (1) 反应生成新的 3-EWG-取代的 2-氨基-5-羟基吲哚 3a-f。用萘醌 (20a) 和杂芳族醌 20b-d 处理 3,3-二氨基丙烯酸乙酯 (2a) 得到 [g] 环化的 2-氨基吲哚-3-羧酸盐 21a-d。
• Tacripyrines, the First Tacrine−Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer’s Disease
  作者：José Marco-Contelles、Rafael León、Cristóbal de los Ríos、Abdelouahid Samadi、Manuela Bartolini、Vincenza Andrisano、Oscar Huertas、Xavier Barril、F. Javier Luque、María I. Rodríguez-Franco、Beatriz López、Manuela G. López、Antonio G. García、María do Carmo Carreiras、Mercedes Villarroya

  DOI：10.1021/jm801292b

  日期：2009.5.14

  Tacripyrines (1-14) have been designed by combining an ACNE inhibitor (tacrine) with a calcium antagonist such as nimodipine and are targeted to develop a multitarget therapeutic strategy to confront AD. Tacripyrines are selective and potent ACNE inhibitors in the nanomolar range. The mixed type inhibition of hAChE activity of compound 11 (IC50 105 +/- 15 nM) is associated to a 30.7 +/- 8.6% inhibition of the proaggregating action of ACNE on the A beta and a moderate inhibition of A beta self-aggregation (34.9 +/- 5.4%). Molecular modeling indicates that binding of compound 11 to the ACNE PAS mainly involves the (R)-11 enantiomer, which also agrees with the noncompetitive inhibition mechanism exhibited by p-methoxytacripyrine 11. Tacripyrines are neuroprotective agents, show moderate Ca2+ channel blocking effect, and cross the blood-brain barrier, emerging as lead candidates for treating AD.