4-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]butanol | 351016-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]butanol
• 英文别名: 4-{N-[2-(Trimethylsilyl)ethoxycarbonyl]amino}butanol；2-(trimethyisilyl)ethyl (4-hydroxybutyl)carbamate；2-(trimethylsilyl)ethyl (4-hydroxybutyl)carbamate；4-[2-(trimethylsilyl)ethoxycarbonylamino]butanol；2-(trimethylsilyl)ethyl 4-hydroxybutylcarbamate；N-teoc-4-aminobutan-1-ol；2-trimethylsilylethyl N-(4-hydroxybutyl)carbamate
• CAS: 351016-76-7
• 化学式: C₁₀H₂₃NO₃Si
• 分子量: 233.383
• InChiKey: ZOUMJJOXSHAXSH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.4±27.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]butanol 在 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.41h， 生成 tert-butyl (S)-4-(7-(8-chloronaphthalen-1-yl)-2-(((S)-1-(4-(((2-(trimethylsilyl)ethoxy)carbonyl)amino)butyl)pyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-2-(cyanomethyl)piperazine-1-carboxylate
  参考文献：
  名称：

  [EN] NOVEL BIFUNCTIONAL MOLECULES FOR TARGETED PROTEIN DEGRADATION
  [FR] NOUVELLES MOLÉCULES BIFONCTIONNELLES POUR LA DÉGRADATION CIBLÉE DE PROTÉINES

  摘要：

  本公开涉及一种新型的双功能分子，可用于有针对性或选择性地降解蛋白质。

  公开号：

  WO2022129925A1
• 作为产物：
  描述：

  4-氨基-1-丁醇 、 对硝基苯基三甲基硅乙基碳酸酯 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 以90%的产率得到4-[N-[2-(trimethylsilyl)ethoxycarbonyl]amino]butanol
  参考文献：
  名称：

  Stromgaard, Kristian; Andersen, Kim; Ruhland, Thomas, Synthesis, 2001, # 6, p. 877 - 884

  摘要：

  DOI：

文献信息

• Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis
  作者：Alyssa H. Antropow、Kun Xu、Rachel J. Buchsbaum、Mohammad Movassaghi

  DOI：10.1021/acs.joc.7b01162

  日期：2017.8.4

  doses. Herein, we discuss the increased potency of (−)-agelastatin E as compared to (−)-agelastatin A in this capacity, in addition to identification of new agelastatin derivatives with activity that is statistically equivalent to (−)-agelastatin E. The chemistry described in this report provides a platform for the rapid synthesis of agelastatin derivatives with excellent potency (50–100 nM) as modulators

  描述了新的astlastatin生物碱衍生物的合成及其在乳腺癌微环境中的抗癌作用。通过应用我们的策略，从常见的硫代酯与适当取代的尿素和醇组分聚合合成咪唑啉酮，可获得各种N1-烷基和C5醚-阿格拉斯汀衍生物。在我们的三维共培养测定法中评估了这些astlastatin衍生物对乳腺成纤维细胞对相关乳腺癌细胞的影响。我们已经发现，以非细胞毒性剂量，阿司他汀生物碱是有效的癌症侵袭和转移调节剂。在此，我们讨论了与（-）-agelastatin A相比，（-）-agelastatin E具有更高的效力，
• [EN] POTENT AGELASTATIN DERIVATIVES AS MODULATORS FOR CANCER INVASION AND METASTASIS<br/>[FR] DÉRIVÉS D'AGÉLASTATINE PUISSANTS EN TANT QUE MODULATEURS DE L'INVASION ET DE LA MÉTASTASE DU CANCER
  申请人：MOVASSAGHI MOHAMMAD

  公开号：WO2018209239A1

  公开（公告）日：2018-11-15

  The present disclosure relates to derivatized agelastatin compounds and methods for the treatment, prevention, or delay of cancer, comprising administering a therapeutically effect amount of the derivatized agelastatin compounds, a pharmaceutically acceptable salt thereof, or a composition thereof to a subject in need thereof. Methods for making the derivatized agelastatin compounds are also provided.

  本公开涉及衍生的阿格拉斯塔丁化合物以及用于治疗、预防或延迟癌症的方法，包括向需要的受试者施用治疗效果量的衍生的阿格拉斯塔丁化合物、其药学可接受的盐或其组合物。还提供了制备衍生的阿格拉斯塔丁化合物的方法。
• Protolytic properties of polyamine wasp toxin analogues studied by13C NMR spectroscopy
  作者：Kristian Strømgaard、Lorna Piazzi、Christian A. Olsen、Henrik Franzyk、Jerzy W. Jaroszewski

  DOI：10.1002/mrc.1890

  日期：2006.11

  Acid–base properties of the natural polyamine wasp toxin PhTX‐433 (1) and seven synthetic analogues [PhTX‐343 (2), PhTX‐334 (3), PhTX‐443 (4), PhTX‐434 (5), PhTX‐344 (6), PhTX‐444 (7), and PhTX‐333 (8)], each having four protolytic sites, were characterized by 13C NMR spectroscopy. Nonlinear, multiparameter, simultaneous fit of all chemical shift data obtained from the NMR titration curves yielded

  天然多胺黄蜂毒素 PhTX-433 (1) 和七种合成类似物 [PhTX-343 (2), PhTX-334 (3), PhTX-443 (4), PhTX-434 (5), PhTX 的酸碱特性‐344 (6)、PhTX-444 (7) 和 PhTX-333 (8)]，每个都有四个质子分解位点，通过 13C NMR 光谱进行表征。从 NMR 滴定曲线获得的所有化学位移数据的非线性、多参数、同时拟合产生宏观 pKa 值以及所有不同质子化宏观物种的固有化学位移数据。化学位移数据的分析表明所有四个位点之间存在强相互作用，并提供了化学位移值与质子化状态之间复杂关系的信息。完全质子化形式的去质子化始于多胺部分的中心氨基，这种趋势的程度取决于与侧翼质子化氨基的距离。1–8 的 pKa1 值在 8.2–9.4 的范围内。因此，一些毒素在 pH 和离子强度条件下不完全质子化，用于评估它们与离子型谷氨酸和
• Solid-Phase Synthesis of Polyamine Toxin Analogues:  Potent and Selective Antagonists of Ca²⁺-Permeable AMPA Receptors
  作者：Hasse Kromann、Sonata Krikstolaityte、Anne J. Andersen、Kim Andersen、Povl Krogsgaard-Larsen、Jerzy W. Jaroszewski、Jan Egebjerg、Kristian Strømgaard

  DOI：10.1021/jm020314s

  日期：2002.12.1

  The wasp toxin philanthotoxin-433 (PhTX-433) is a nonselective and noncompetitive antagonist of ionotropic receptors, such as ionotropic glutamate receptors and nicotinic acetylcholine receptors. Polyamine toxins are extensively used for the characterization of subtypes of ionotropic glutamate receptors, in particular Ca2+-permeable AMPA and kainate receptors. We have previously shown that an analogue of PhTX-433 with one of the amino groups replaced by a methylene group, philanthotoxin-83 (PhTX-83) is a selective and potent antagonist of AMPA receptors. We now describe the solid-phase synthesis of analogues of PhTX-83 and the electrophysiological characterization of these analogues on cloned AMPA and kainate receptors. The polyamine portion of PhTX-83 was modified systematically by chaniging the position. of the. secondary amino group along the polyamine chain. In another series of analogues, the acyl moiety of PhTX-83 was replaced by acids of different size and lipophilicity. Using electrophysiological techniques, PhTX-56 was shown to be a highly potent (K-i = 3.3 +/- 0.78 nM) and voltage-dependent antagonist of homomeric GluR1 receptors and was more than 1000-fold less potent when tested on heteromeric GluR1+GluR2, as well as homomeric GluR5(Q) receptors, thus being selective for Ca2+-permeable AMPA receptors. Variation of the acyl group of PhTX-83 had only minor effect on antagonist potency at homomeric GluR receptors but led to a significant decrease in the voltage-dependence. In conclusion, PhTX-56 is a novel, very potent, and selective antagonist of Ca2+-permeable AMPA receptors and is a promising tool for structure/function studies of the ion channel of the AMPA receptor.
• General Synthesis of β-Alanine-Containing Spider Polyamine Toxins and Discovery of <i>Nephila</i> Polyamine Toxins 1 and 8 as Highly Potent Inhibitors of Ionotropic Glutamate Receptors
  作者：Simon Lucas、Mette H. Poulsen、Niels G. Nørager、Anne F. Barslund、Tinna B. Bach、Anders S. Kristensen、Kristian Strømgaard

  DOI：10.1021/jm301255m

  日期：2012.11.26

  Certain spiders contain large pools of polyamine toxins, which are putative pharmacological fools awaiting further discovery. Here we present a general synthesis strategy for this class of-toxins and prepare five structurally varied polyamine toxins. Electrophysiological testing at three ionotropic glutamate receptor subtypes reveals that two of these, Nephila polyamine toxins 1 (NPTX-1) and 8 (NPTX-8), comprise intriguing pharmacological activities by having subnanomolar IC50 values at kainate receptors.