N-(2-氨基乙基)-2-(1-萘)乙酰胺 | 36321-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(2-氨基乙基)-2-(1-萘)乙酰胺
• 中文别名: N-(2-氨基乙基)-1-萘乙酰胺；萘甲唑啉EP杂质A
• 英文名称: N-(1-naphthylacetyl)ethylenediamine
• 英文别名: [1]naphthyl-acetic acid-(2-amino-ethylamide)；[1]Naphthyl-essigsaeure-(2-amino-aethylamid)；N-(2-Aminoethyl)-1-naphthylacetamide；N-(2-aminoethyl)-2-naphthalen-1-ylacetamide
• CAS: 36321-43-4
• 化学式: C₁₄H₁₆N₂O
• mdl: MFCD08529471
• 分子量: 228.294
• InChiKey: OJWZEVNPRJDAME-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96°C
• 沸点：
  491.7±38.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存条件：2-8℃，避光、干燥且密封保存。

反应信息

• 作为反应物：
  描述：

  N-(2-氨基乙基)-2-(1-萘)乙酰胺 在 哌啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 N-(4-((2-(2-(naphthalen-1-yl)acetamido)ethyl)carbamoyl)piperidin-4-yl)-6-(trifluoromethyl)nicotinamide
  参考文献：
  名称：

  Exploration of N-(2-aminoethyl)piperidine-4-carboxamide as a potential scaffold for development of VEGFR-2, ERK-2 and Abl-1 multikinase inhibitor

  摘要：

  VEGFR, ERK and Abl had been respectively identified as good drug targets, and their crosstalk also had been well elaborated. Multitarget drugs were more advantageous for cancer treatment, however, no inhibitors simultaneously acting on the three proteins were developed due to their structural diversities. Herein, N-(4-((2-(2-(naphthaen-1-yl)acetamido)ethyl)carbamoyl)piperidin-4-yl)-6-(trifluoromethyl)nicotinamide (NEPT, 6a) was discovered as an active scaffold against VEGFR-2, ERK-2 and Abl-1 kinases through the combination of support vector machine, similarity searching and molecular docking. NEPT and its derivatives were synthesized by convenient routine, their in vitro anti-proliferative abilities against human liver cancer cell line HepG2 were preliminarily evaluated. A representative compound 6b showed an IC50 value of 11.3 mu M and induced significant HepG2 cells apoptosis. Besides, these compounds displayed better anti-proliferative abilities against 1(562 cells (a cell line with typical hyperactivity of the above multikinases), for example compound 6b exhibited an IC50 value of 4.5 mu M. Based on hepatotoxicity case reports of Abl inhibitors, cytotoxicity of synthetic compounds against normal liver cell lines (QSG7701 and HL7702) was studied, 6b had a similar toxic effect with positive control imatinib, and most compounds showed less than 35% inhibition activities at 100 mu M. Molecular docking study disclosed interactions of 6b with VEGFR-2, ERK-2 and Abl-1 kinases, respectively. Our data suggested the biological activities of 6b may derived from collaborative effects of VEGFR-2, ERK-2 and Abl-1 inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.026
• 作为产物：
  描述：

  萘甲唑林 在 水 作用下， 生成 N-(2-氨基乙基)-2-(1-萘)乙酰胺
  参考文献：
  名称：

  咪唑啉酮类药物

  摘要：

  巴塞尔（Lesung）地区的瓦森（Wäsend）和塞尔布斯特（WährendImidazolinsalze）Versuchen位于Übereinstimmungmitfrüheren，位于Umsetzungen der Imidazoline meist的衍生品，也可作为Verringdungen gewonnen werden的衍生成分。叔丁草根，单乙酰基衍生物，咪唑啉，大豆新乙酰基和二苯甲酰基-Verbindungen，高级外环试剂，咪唑啉林，多巴胺联素，zu halhalten。Ferner konnte ein亚硝唑类化合物Imidazolins dargestellt werden。Eserwies sich aber alsunmöglich，mit Kaliumcyanat oder -thiocyanat die entsprechenden Harnstoffe ringgeschlossener

  DOI：

  10.1002/hlca.19510340102

文献信息

• Schwartz et al., Journal of the American Pharmaceutical Association (1912), 1956, vol. 45, p. 814,816
  作者：Schwartz et al.

  DOI：——

  日期：——
• Exploration of N-(2-aminoethyl)piperidine-4-carboxamide as a potential scaffold for development of VEGFR-2, ERK-2 and Abl-1 multikinase inhibitor
  作者：Feng Jin、Dan Gao、Qin Wu、Feng Liu、Yuzong Chen、Chunyan Tan、Yuyang Jiang

  DOI：10.1016/j.bmc.2013.07.026

  日期：2013.9

  VEGFR, ERK and Abl had been respectively identified as good drug targets, and their crosstalk also had been well elaborated. Multitarget drugs were more advantageous for cancer treatment, however, no inhibitors simultaneously acting on the three proteins were developed due to their structural diversities. Herein, N-(4-((2-(2-(naphthaen-1-yl)acetamido)ethyl)carbamoyl)piperidin-4-yl)-6-(trifluoromethyl)nicotinamide (NEPT, 6a) was discovered as an active scaffold against VEGFR-2, ERK-2 and Abl-1 kinases through the combination of support vector machine, similarity searching and molecular docking. NEPT and its derivatives were synthesized by convenient routine, their in vitro anti-proliferative abilities against human liver cancer cell line HepG2 were preliminarily evaluated. A representative compound 6b showed an IC50 value of 11.3 mu M and induced significant HepG2 cells apoptosis. Besides, these compounds displayed better anti-proliferative abilities against 1(562 cells (a cell line with typical hyperactivity of the above multikinases), for example compound 6b exhibited an IC50 value of 4.5 mu M. Based on hepatotoxicity case reports of Abl inhibitors, cytotoxicity of synthetic compounds against normal liver cell lines (QSG7701 and HL7702) was studied, 6b had a similar toxic effect with positive control imatinib, and most compounds showed less than 35% inhibition activities at 100 mu M. Molecular docking study disclosed interactions of 6b with VEGFR-2, ERK-2 and Abl-1 kinases, respectively. Our data suggested the biological activities of 6b may derived from collaborative effects of VEGFR-2, ERK-2 and Abl-1 inhibition. (C) 2013 Elsevier Ltd. All rights reserved.
• Über einige Reaktionen des Imidazolinringes
  作者：K. Miescher、A. Marxer、E. Urech

  DOI：10.1002/hlca.19510340102

  日期：——

  Während Imidazolinsalze in wässeriger und selbst in saurer Lösung beständig sind, werden die freien Basen leicht aufgespalten. In Übereinstimmung mit früheren Versuchen liess sich zeigen, dass bei Umsetzungen der Imidazoline meist Derivate ringoffener Verbindungen gewonnen werden. Unter vorsichtigen Bedingungen gelang es nun aber, Monoacetyl-Derivate der Imidazoline, sowie neuartige Diacetyl- und

  巴塞尔（Lesung）地区的瓦森（Wäsend）和塞尔布斯特（WährendImidazolinsalze）Versuchen位于Übereinstimmungmitfrüheren，位于Umsetzungen der Imidazoline meist的衍生品，也可作为Verringdungen gewonnen werden的衍生成分。叔丁草根，单乙酰基衍生物，咪唑啉，大豆新乙酰基和二苯甲酰基-Verbindungen，高级外环试剂，咪唑啉林，多巴胺联素，zu halhalten。Ferner konnte ein亚硝唑类化合物Imidazolins dargestellt werden。Eserwies sich aber alsunmöglich，mit Kaliumcyanat oder -thiocyanat die entsprechenden Harnstoffe ringgeschlossener