N,N-diethyl-N-[(4E)-5-(tributylstannyl)-4-pentenyl]amine | 681248-13-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diethyl-N-[(4E)-5-(tributylstannyl)-4-pentenyl]amine
• 英文别名: diethyl[E-5-(tributylstannyl)-4-penten-1-yl]amine；(E)-N,N-diethyl-5-tributylstannylpent-4-en-1-amine
• CAS: 681248-13-5
• 化学式: C₂₁H₄₅NSn
• 分子量: 430.305
• InChiKey: STNYTCRMBWPNEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-N-[(4E)-5-(tributylstannyl)-4-pentenyl]amine 在 palladium on activated charcoal 二(三叔丁基膦)钯 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 methyl 2-[(1{2-[5-(diethylamino)pentyl]phenyl}sulfonyl)amino]-5,6,7,8-tetrahydro-1-naphthalenecarboxylate
  参考文献：
  名称：

  Discovery and Optimization of Anthranilic Acid Sulfonamides as Inhibitors of Methionine Aminopeptidase-2:  A Structural Basis for the Reduction of Albumin Binding

  摘要：

  Methionine aminopeptidase-2 (MetAP2) is a novel target for cancer therapy. As part of an effort to discover orally active reversible inhibitors of MetAP2, a series of anthranilic acid sulfonamides with micromolar affinities for human MetAP2 were identified using affinity selection by mass spectrometry (ASMS) screening. These micromolar hits were rapidly improved to nanomolar leads on the basis of insights from protein crystallography; however, the compounds displayed extensive binding to human serum albumin and had limited activity in cellular assays. Modifications based on structural information on the binding of lead compounds to both MetAP2 and domain III of albumin allowed the identification of compounds with significant improvements in both parameters, which showed good cellular activity in both proliferation and methionine processing assays.

  DOI：

  10.1021/jm0601001
• 作为产物：
  描述：

  三正丁基氢锡 、 1-Diaethylamino-pentin-(4) 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 N,N-diethyl-N-[(4E)-5-(tributylstannyl)-4-pentenyl]amine 、 N,N-diethyl-N-[(4Z)-5-(tributylstannyl)-4-pentenyl]amine
  参考文献：
  名称：

  Sulfonamides having antiangiogenic and anticancer activity

  摘要：

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。

  公开号：

  US20040167128A1

文献信息

• Sulfonamides having antiangiogenic and anticancer activity
  申请人：——

  公开号：US20040167128A1

  公开（公告）日：2004-08-26

  Compounds having methionine aminopeptidase-2 inhibitory (MetAP2) are described. Also described are pharmaceutical compositions comprising the compounds, methods of treatment using the compounds, methods of inhibiting angiogenesis, and methods of treating cancer.

  描述了具有蛋氨酸氨基肽酶-2抑制剂（MetAP2）的化合物。还描述了包括这些化合物的药物组合物、使用这些化合物的治疗方法、抑制血管生成的方法以及治疗癌症的方法。
• PREPARATION OF 7-ALKENYL-3 QUINOLINECARBONITRILES VIA A PALLADIUM MEDIATED COUPLING REACTION
  申请人：Wang Yanong Daniel

  公开号：US20090099356A1

  公开（公告）日：2009-04-16

  The present invention is directed to a process for preparing compounds of formula (I): wherein A, R 1 -R 3 , X, s, t, u, m and Z are defined herein, comprising the step of reacting a reagent of formula (II): in the presence of Pd(O) metal with a compound of formula (III): or salts thereof. Another aspect of this invention is a method of preparing compounds of formula (VI).

  本发明涉及一种制备化合物的方法，其化学式如下（I）：其中A、R1-R3、X、s、t、u、m和Z在此处定义，包括以下步骤：在Pd（O）金属存在下，将化学式（II）的试剂与化学式（III）的化合物或其盐反应。本发明的另一个方面是制备化合物的方法，其化学式为（VI）。
• 4-Anilino-7-alkenylquinoline-3-carbonitriles as potent MEK1 kinase inhibitors
  作者：Dan M. Berger、Minu Dutia、Dennis Powell、Middleton B. Floyd、Nancy Torres、Robert Mallon、Donald Wojciechowicz、Steven Kim、Larry Feldberg、Karen Collins、Inder Chaudhary

  DOI：10.1016/j.bmc.2008.09.009

  日期：2008.10

  A series of substituted 7-alkenyl 4[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-3-quinolinecarbonitrile analogs were synthesized and evaluated as MEK1 kinase inhibitors. The synthetic details, structure-activity relationships, biological activity, and selected oral exposure studies of these analogs are described. From these studies, compound 5m was chosen as a strong candidate for further evaluation. The selectivity of 5m was ascertained against a panel of 17 kinases, where activity was observed against EGFR, Src, Lyn, and IR kinases. Western blot studies in WM-266 cells demonstrated that 5m inhibited phosphorylation of ERK, while additional kinase pathways tested showed no inhibition at up to 10 mu M of 5m. PK studies, as well as a xenograft and in vivo biomarker studies are described for 5m. (C) 2008 Elsevier Ltd. All rights reserved.
• Discovery and Optimization of Anthranilic Acid Sulfonamides as Inhibitors of Methionine Aminopeptidase-2:  A Structural Basis for the Reduction of Albumin Binding
  作者：George S. Sheppard、Jieyi Wang、Megumi Kawai、Steve D. Fidanze、Nwe Y. BaMaung、Scott A. Erickson、David M. Barnes、Jason S. Tedrow、Lawrence Kolaczkowski、Anil Vasudevan、David C. Park、Gary T. Wang、William J. Sanders、Robert A. Mantei、Fabio Palazzo、Lora Tucker-Garcia、Pingping Lou、Qian Zhang、Chang H. Park、Ki H. Kim、Andrew Petros、Edward Olejniczak、David Nettesheim、Phillip Hajduk、Jack Henkin、Richard Lesniewski、Steven K. Davidsen、Randy L. Bell

  DOI：10.1021/jm0601001

  日期：2006.6.1

  Methionine aminopeptidase-2 (MetAP2) is a novel target for cancer therapy. As part of an effort to discover orally active reversible inhibitors of MetAP2, a series of anthranilic acid sulfonamides with micromolar affinities for human MetAP2 were identified using affinity selection by mass spectrometry (ASMS) screening. These micromolar hits were rapidly improved to nanomolar leads on the basis of insights from protein crystallography; however, the compounds displayed extensive binding to human serum albumin and had limited activity in cellular assays. Modifications based on structural information on the binding of lead compounds to both MetAP2 and domain III of albumin allowed the identification of compounds with significant improvements in both parameters, which showed good cellular activity in both proliferation and methionine processing assays.