2-cyano-N-{3-[(2-cyanoacetylamino)methyl]benzyl}acetamide

• 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: 2-cyano-N-{3-[(2-cyanoacetylamino)methyl]benzyl}acetamide
• 英文别名: N,N′-(1,3-phenylenebis(methylene))bis(2-cyanoacetamide)；2-cyano-N-[[3-[[(2-cyanoacetyl)amino]methyl]phenyl]methyl]acetamide
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: OAILHOJNAFVEFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N-{3-[(2-cyanoacetylamino)methyl]benzyl}acetamide 在 哌啶 、 乙酸酐 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  双发色花青染料在自组装和折叠途径之间的间隔基调节区分。

  摘要：

  我们已经合成了一系列具有不同间隔单元的双（氰基花青）染料，并通过浓度和溶剂依赖性的UV / Vis光谱详细研究了它们的自组织行为。我们的深入研究表明，目前的双（硫氰酸）染料的自组织受到间隔单元本质的影响。刚性间隔基的利用导致具有高结合强度的自缔合双分子复合物的形成，而柔性间隔基将各自的双色染料驱动到分子内折叠。我们对烷基间隔链长度对本系列双（硫氰酸菁）染料的折叠趋势的影响进行的深入研究显示出一种双相行为，即，这些染料的折叠的G）值。此外，基于激子理论和量子化学计算对聚集体的光学性质的分析表明，具有刚性间隔基的染料具有双分子聚集体结构，具有间隔单元少于七个的双（硫氰酸）染料的双分子旋转褶状结构碳原子，而更长烷基链接头（≥C7）的应用则提供了足够的灵活性，使发色团以静电最有利的反平行方式取向。

  DOI：

  10.1002/chem.201502434
• 作为产物：
  描述：

  间苯二甲胺 、 氰乙酸甲酯 以 neat (no solvent) 为溶剂， 反应 4.0h， 生成 2-cyano-N-{3-[(2-cyanoacetylamino)methyl]benzyl}acetamide
  参考文献：
  名称：

  双发色花青染料在自组装和折叠途径之间的间隔基调节区分。

  摘要：

  我们已经合成了一系列具有不同间隔单元的双（氰基花青）染料，并通过浓度和溶剂依赖性的UV / Vis光谱详细研究了它们的自组织行为。我们的深入研究表明，目前的双（硫氰酸）染料的自组织受到间隔单元本质的影响。刚性间隔基的利用导致具有高结合强度的自缔合双分子复合物的形成，而柔性间隔基将各自的双色染料驱动到分子内折叠。我们对烷基间隔链长度对本系列双（硫氰酸菁）染料的折叠趋势的影响进行的深入研究显示出一种双相行为，即，这些染料的折叠的G）值。此外，基于激子理论和量子化学计算对聚集体的光学性质的分析表明，具有刚性间隔基的染料具有双分子聚集体结构，具有间隔单元少于七个的双（硫氰酸）染料的双分子旋转褶状结构碳原子，而更长烷基链接头（≥C7）的应用则提供了足够的灵活性，使发色团以静电最有利的反平行方式取向。

  DOI：

  10.1002/chem.201502434

文献信息

• Enhanced photocurrent generation by folding-driven H-aggregate formation
  作者：André Zitzler-Kunkel、Martin R. Lenze、Klaus Meerholz、Frank Würthner

  DOI：10.1039/c3sc50263e

  日期：——

  A novel bis(merocyanine) dye has been synthesized and its folding and aggregation behavior has been elucidated in dependence on the solvent polarity. Extended cofacially π-stacked H-aggregates could be prepared in nonpolar solvents based on the preorganized folded dimer structure of the dye exhibiting a more than 120 nm hypsochromic shift of the absorption band. Furthermore, incorporation of such H-aggregate domains in bulk heterojunction (BHJ) solar cells by careful adjustment of processing conditions afforded a nearly twofold increase in the photocurrent generation. Our detailed investigations on the external quantum efficiencies of these blends reveal that the increase of the short-circuit current density JSC stems from the H-aggregated dye manifold in the photoactive layer of the solar cell devices.

  一种新型双（氰菁）染料已经合成，其折叠和聚集行为已经阐明，取决于溶剂的极性。在非极性溶剂中，基于染料预先折叠的双聚体结构，可以制备扩展的共价π堆积H聚集体，其吸收带具有超过120 nm的色散位移。此外，通过仔细调整加工条件，将这种H聚集体域掺入到异质结太阳能电池（BHJ）中，可以产生近两倍的电流。我们对这些混合物外部量子效率的详细研究表明，短路电流密度JSC的增加源于太阳能电池器件光活性层中的H聚集染料。
• Degrasyn-like symmetrical compounds: Possible therapeutic agents for multiple myeloma (MM-I)
  作者：Zhenghong Peng、David S. Maxwell、Duoli Sun、Basvoju A. Bhanu Prasad、Paul T. Schuber、Ashutosh Pal、Yunming Ying、Dongmei Han、Liwei Gao、Shimei Wang、Alexander Levitzki、Vaibhav Kapuria、Moshe Talpaz、Matthew Young、Hollis D. Showalter、Nicholas J. Donato、William G. Bornmann

  DOI：10.1016/j.bmc.2013.12.048

  日期：2014.2

  A series of degrasyn-like symmetrical compounds have been designed, synthesized, and screened against B cell malignancy (multiple myeloma, mantle cell lymphoma) cell lines. The lead compounds T5165804 and CP2005 showed higher nanomolar potency against these tumor cells in comparison to degrasyn and inhibited Usp9x activity in vitro and in intact cells. These observations suggest that this new class of compounds holds promise as cancer therapeutic agents. (C) 2014 Published by Elsevier Ltd.
• Small Molecule Inhibitors of Dynamin I GTPase Activity:  Development of Dimeric Tyrphostins
  作者：Timothy Hill、Luke R. Odell、Jennifer K. Edwards、Mark E. Graham、Andrew B. McGeachie、Jenny Rusak、Annie Quan、Ruben Abagyan、Janet L. Scott、Phillip J. Robinson、Adam McCluskey

  DOI：10.1021/jm040208l

  日期：2005.12.1

  Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a mu M potent lead, 2-cyano-3-(3,4-dihydroxyphenyl)thioacrylamide (1, IC50 70 mu M). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low mu M potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 +/- 0.6 mu M), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 +/- 0.2 mu M), and the corresponding 3-methyl ether (11) (IC50 = 9 3 mu M). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50'S of 1.7 0.2, 1.7 0.2, and 5 +/- 1 mu M, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50'S of 42 3, 38 2, and 61 2 mu M, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.
• Tyrphostins. 6. Dimeric Benzylidenemalononitrile Tyrphostins:  Potent Inhibitors of EGF Receptor Tyrosine Kinase <i>in Vitro</i>
  作者：Aviv Gazit、Nir Osherov、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm960225d

  日期：1996.1.1

  Benzylidenemalononitrile (BMN) tyrphostins were previously found to be potent inhibitors of EGF receptor (EGFR) tyrosine kinase activity. Since these compounds were found to compete for the substrate and sometimes with the ATP site and since EGFR acts as a dimer, we prepared a series of dimeric tyrphostins. These dimeric tyrphostins were built from two BMN units linked by various spacers and designed to fit the dimeric cross-autophosphorylation signal transduction intermediate of the EGFR tyrosine kinases. Structure-activity relationship of these potent dimeric EGF receptor tyrosine kinase inhibitors is reported.
• Spacer-Modulated Differentiation Between Self-Assembly and Folding Pathways for Bichromophoric Merocyanine Dyes
  作者：André Zitzler-Kunkel、Eva Kirchner、David Bialas、Christian Simon、Frank Würthner

  DOI：10.1002/chem.201502434

  日期：2015.10.12

  We have synthesized a large series of bis(merocyanine) dyes with varying spacer unit and investigated in detail their self‐organization behavior by concentration‐ as well as solvent‐dependent UV/Vis spectroscopy. Our in‐depth studies have shown that the self‐organization of the present bis(merocyanine) dyes is subtly influenced by the nature of the spacer unit. The utilization of rigid spacers results

  我们已经合成了一系列具有不同间隔单元的双（氰基花青）染料，并通过浓度和溶剂依赖性的UV / Vis光谱详细研究了它们的自组织行为。我们的深入研究表明，目前的双（硫氰酸）染料的自组织受到间隔单元本质的影响。刚性间隔基的利用导致具有高结合强度的自缔合双分子复合物的形成，而柔性间隔基将各自的双色染料驱动到分子内折叠。我们对烷基间隔链长度对本系列双（硫氰酸菁）染料的折叠趋势的影响进行的深入研究显示出一种双相行为，即，这些染料的折叠的G）值。此外，基于激子理论和量子化学计算对聚集体的光学性质的分析表明，具有刚性间隔基的染料具有双分子聚集体结构，具有间隔单元少于七个的双（硫氰酸）染料的双分子旋转褶状结构碳原子，而更长烷基链接头（≥C7）的应用则提供了足够的灵活性，使发色团以静电最有利的反平行方式取向。