N-benzoyl-N'-<(benzyloxy)carbonyl>ethylenediamine | 77153-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-N'-<(benzyloxy)carbonyl>ethylenediamine
• 英文别名: benzyl 2-benzamidoethylcarbamate；benzyl N-(2-benzamidoethyl)carbamate
• CAS: 77153-06-1
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: UDQWSSUISOKTBK-UHFFFAOYSA-N

物化性质

• 沸点：
  555.6±43.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-N'-<(benzyloxy)carbonyl>ethylenediamine 在 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 N-(2-((4-(6-(3-fluorophenyl)imidazo[2,1-b]thiazol-5-yl)pyrimidin-2-yl)amino)ethyl)benzamide
  参考文献：
  名称：

  Anti-inflammatory effect of 3-fluorophenyl pyrimidinylimidazo[2,1-b]thiazole derivatives as p38α inhibitors

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106716
• 作为产物：
  描述：

  2-苄氧羰基氨基-1-乙醇 在 sodium azide 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 N-benzoyl-N'-<(benzyloxy)carbonyl>ethylenediamine
  参考文献：
  名称：

  设计和合成靶向V600EBRAF的新型吡咯并[2,3-b]吡啶衍生物。

  摘要：

  几种基于吡咯并[2,3-b]吡啶的B-RAF抑制剂是众所周知的，其中一些目前已被FDA批准用作抗癌剂。根据这些FDA批准的V600EB-RAF抑制剂的结构，设计并合成了两个系列的吡咯并[2,3-b]吡啶骨架，以开发新的有效V600EB-RAF抑制剂。对38种合成化合物的单次剂量（10μM）的V600EB-RAF抑制作用进行了生物学评估。测试了具有高抑制百分数的化合物，以测定其相对于V600EB-RAF的IC50。化合物34e和35表现出最高的抑制作用，IC50值分别为0.085 µM和0.080 µM。为了进行过度的生物学评估，对合成的衍生物进行了六十种不同的人类癌细胞系测试。

  DOI：

  10.1016/j.bmc.2020.115493

文献信息

• Broad-spectrum antiproliferative activity of a series of 6-(4-fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b]thiazole derivatives
  作者：Mohammed S. Abdel-Maksoud、Mohammed I. El-Gamal、Mahmoud M. Gamal El-Din、Seong-Shin Kwak、Hyun-Il Kim、Chang-Hyun Oh

  DOI：10.1007/s00044-016-1529-7

  日期：2016.5

  This article described the synthesis and in vitro antiproliferative activities a series of 6-(4-fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b]thiazole derivatives. The nine target compounds were tested for in vitro antitumor effect against a panel of 55 cell lines of nine different cancer types at the NCI, and their activities were compared with that of Sorafenib as a reference standard

  本文介绍了一系列6-（4-氟苯基）-5-（2-取代的嘧啶-4-基）咪唑并[2,1- b ]噻唑衍生物的合成及体外抗增殖活性。在NCI上测试了这9种目标化合物对55种9种不同癌症类型的细胞系的体外抗肿瘤作用，并将它们的活性与作为参考标准药物的索拉非尼进行了比较。具有末端芳基酰胺部分的化合物1d和1e针对不同的癌细胞系发挥出比索拉非尼更高的效力。两种化合物都比索拉非尼对UO-31肾癌细胞系和MCF7乳腺癌细胞系更有效。化合物1d与Sorafenib相比，它对COLO 205结肠癌细胞的杀伤力更强，化合物1e对OVCAR-3卵巢癌细胞和DU-145前列腺消除细胞的杀伤力也比Sorafenib高。例如，化合物1e对DU-145前列腺癌细胞系的IC 50值为1.04μM，是索拉非尼的三倍。
• Synthesis of New 6-(4-Fluorophenyl)-5-(2-substituted pyrimidin-4-yl)imidazo[2,1-b] thiazole Derivatives and their Antiproliferative Activity against Melanoma Cell Line
  作者：Jin-Hun Park、Chang-Hyun Oh

  DOI：10.5012/bkcs.2010.31.10.2854

  日期：2010.10.20

  Synthesis of a new series of pyrimidinyl-imidazo(2,1-b)thiazole derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the pyrimidinyl ring side chain was investigated. The biological results indicated that most of the newly synthesized compounds showed mo- derate activity against A375, compared with Sorafenib. Among

  描述了一系列新的嘧啶基-咪唑(2,1-b)噻唑衍生物的合成。测试了它们对 A375 人黑色素瘤细胞系的抗增殖活性，并研究了取代基对嘧啶环侧链的影响。生物学结果表明，与索拉非尼相比，大多数新合成的化合物对 A375 具有中等活性。在所有这些衍生物中，环状磺酰胺衍生物 IIIa、IIIb 和 IIIe 对 A375 人黑色素瘤细胞系显示出最有效的抗增殖活性。化合物 IIIa、b 的 IC50 值为纳摩尔级。此外，与索拉非尼 (IC50 = 5.6 µM) 相比，化合物 IIIe (IC50 = 1.9 µM) 也显示出更有效的抗增殖活性。
• Acylation of dibasic compounds containing amino amidine and aminoguanidine functions
  作者：Peter L. Barker、Paul L. Gendler、Henry Rapoport

  DOI：10.1021/jo00325a006

  日期：1981.6
• New imidazo[2,1-b]thiazole derivatives: Synthesis, in vitro anticancer evaluation, and in silico studies
  作者：Jin-Hun Park、Mohammed I. El-Gamal、Yong Sup Lee、Chang-Hyun Oh

  DOI：10.1016/j.ejmech.2011.08.024

  日期：2011.12

  A series of 18 new imidazo[2,1-b]thiazole derivatives was synthesized. Their in vitro antiproliferative activities against A375P human melanoma cell line and NCI-60 cell line panel were tested. Compounds 15, 16, 18, 22, 26-28, and 31 showed superior potency against A375P to sorafenib. In addition, compounds 26 and 27 showed selectivity toward melanoma cell lines than for other cancer types. Both compounds exerted sub-micromolar IC50 values over 7 (including A375P) and 6 melanoma cell lines, respectively. in silico studies are also reported. ADME profiling, in silico toxicity, drug-likeness, and drug-score data of compounds 26 and 27 are promising. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Imidazothiazole-based potent inhibitors of V600E-B-RAF kinase with promising anti-melanoma activity: biological and computational studies
  作者：Hanan S. Anbar、Mohammed I. El-Gamal、Hamadeh Tarazi、Bong S. Lee、Hong R. Jeon、Dow Kwon、Chang-Hyun Oh

  DOI：10.1080/14756366.2020.1819260

  日期：2020.1.1

  A series of imidazothiazole derivatives possessing potential activity against melanoma cells were investigated for molecular mechanism of action. The target compounds were tested against V600E-B-RAF and RAF1 kinases. Compound1zbis the most potent against both kinases with IC(50)values 0.978 and 8.2 nM, respectively. It showed relative selectivity against V600E mutant B-RAF kinase. Compound1zbwas also tested against four melanoma cell lines and exerted superior potency (IC(50)0.18-0.59 mu M) compared to the reference standard drug, sorafenib (IC(50)1.95-5.45 mu M). Compound1zbdemonstrated also prominent selectivity towards melanoma cells than normal skin cells. It was further tested in whole-cell kinase assay and showed in-cell V600E-B-RAF kinase inhibition with IC(50)of 0.19 mu M. Compound1zbinduces apoptosis not necrosis in the most sensitive melanoma cell line, UACC-62. Furthermore, molecular dynamic and 3D-QSAR studies were done to investigate the binding mode and understand the pharmacophoric features of this series of compounds.