benzyl N-[1-(aminomethyl)-3-methyl-butyl]carbamate | 228557-26-4

• 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: benzyl N-[1-(aminomethyl)-3-methyl-butyl]carbamate
• 英文别名: benzyl (S)-(1-amino-4-methylpentan-2-yl)carbamate；benzyl N-[(2S)-1-amino-4-methylpentan-2-yl]carbamate
• CAS: 228557-26-4
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: WXENBUWMJXSQMA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[1-(aminomethyl)-3-methyl-butyl]carbamate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 以4.5 g的产率得到2-甲基-2-丙基[(2S)-1-氨基-3-甲基-2-丁烷基]氨基甲酸酯
  参考文献：
  名称：

  [EN] TREATMENT OF RB-NEGATIVE TUMORS USING TOPOISOMERASE INHIBITORS IN COMBINATION WITH CYCLIN DEPENDENT KINASE 4/6 INHIBITORS
  [FR] TRAITEMENT DE TUMEURS RB-NÉGATIVES EN UTILISANT DES INHIBITEURS DE LA TOPOISOMÉRASE EN ASSOCIATION AVEC DES INHIBITEURS DES KINASES CYCLINE-DÉPENDANTES 4/6

  摘要：

  这项发明涉及改进的治疗组合和方法，用于治疗选择性视网膜母细胞瘤（Rb）阴性癌症和Rb阴性异常细胞增殖障碍，使用特定的拓扑异构酶抑制剂和特定的细胞周期依赖性激酶4/6（CDK4/6）抑制剂。在一个方面，使用本文披露的特定化合物与拓扑异构酶I抑制剂结合，披露了对选择性Rb阴性癌症的改进治疗。

  公开号：

  WO2016040848A1
• 作为产物：
  描述：

  benzyl N-[1-(azidomethyl)-3-methylbutyl]carbamate 在 盐酸 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到benzyl N-[1-(aminomethyl)-3-methyl-butyl]carbamate
  参考文献：
  名称：

  用于肽模拟约束支架合成的新的基于吡咯的氨基酸

  摘要：

  通过微波辅助Paal-Knorr反应衍生自具有功能同源性的相应β-酮酸酯的1-4个酮酸酯，已经制备了一个新的基于吡咯的氨基酸家族。羧基位于吡咯的3位，而受Cbz部分保护的氨基位于1或2位的侧链上。这些化合物用于制备受限的寡肽。

  DOI：

  10.1016/j.tetlet.2005.07.155

文献信息

• Synthesis of Thioureido-Linked Peptidomimetics, Glycosylated Amino Acids, and Neoglycoconjugates Using Bis(benzotriazolyl)methanethione as Thioacylating Agent
  作者：Vommina Sureshbabu、Gundala Chennakrishnareddy、Hosahalli Hemantha

  DOI：10.1055/s-0029-1219393

  日期：2010.3

  A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl)methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by ¹H NMR, ¹³C NMR, and mass spectrometry.

  本文描述了一种实用的硫脲连接肽模拟物、糖基化氨基酸和新生糖缀合物的综合合成方法，采用双（苯并三唑基）甲烷硫酮作为硫羰基化试剂。整个方案温和、高效、产率高，并且不含危险试剂。所有中间体和产物均已分离并通过¹H NMR、¹³C NMR 和质谱完全表征。
• A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics
  作者：Hosahalli P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2009.09.172

  日期：2009.12

  An efficient protocol for the synthesis of a new series of dithiocarbamate-linked peptidomimetics is described. The in situ generated dithiocarbamic acid intermediate formed by the reaction of an amino acid ester and carbon disulfide in the presence of triethylamine was treated with N-protected amino alkyl iodide to afford title compounds 3a–g in good to moderate yields. The synthesis of N-Fmoc-protected

  描述了合成一系列新的二硫代氨基甲酸酯连接的拟肽的有效方案。由氨基酸酯与二硫化碳在三乙胺存在下反应形成的原位生成的二硫代氨基甲酸中间体用N保护的氨基烷基碘处理，以良好至中等的收率得到标题化合物3a – g。还描述了含有两个二硫代氨基甲酸酯键的N -Fmoc保护的三肽模拟物4a – e的合成。该协议被进一步扩展为合成N，N'-正交保护的二硫代氨基甲酸酯连接的二肽模拟物7a – c也一样 温和的反应条件和无毒试剂是本方法的优点。
• Synthesis of Enantiomerically Pure 6-Substituted-Piperazine-2-Acetic Acid Esters as Intermediates for Library Production
  作者：Srinivas Chamakuri、Prashi Jain、Shiva Krishna Reddy Guduru、J. Winston Arney、Kevin R. MacKenzie、Conrad Santini、Damian W. Young

  DOI：10.1021/acs.joc.8b00854

  日期：2018.6.15

  nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient four-step synthesis, chiral amino acids were transformed into 6-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products could be chromatographically separated. From six amino acids (both antipodes), a complete matrix of 24 monoprotected chiral 2,6-disubstituted piperazines

  哌嗪杂环在FDA批准的药物和生物活性化合物中得到广泛利用，但其化学多样性通常仅限于环氮取代，从而使四个碳原子未被充分利用。使用有效的四步合成方法，将手性氨基酸转化为6-取代的哌嗪-2-乙酸酯，为非对映异构体混合物，其色谱图可分离出顺式和反式产物。从六个氨基酸（均为对映体）中，获得了24个单保护的手性2，6-二取代的哌嗪的完整基质，每个基质都为单个绝对立体异构体（克数）。这些多样化且用途广泛的哌嗪可在两个氮原子上进行官能化，
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Discovery of (S)-4-isobutyloxazolidin-2-one as a novel leucyl-tRNA synthetase (LRS)-targeted mTORC1 inhibitor
  作者：Suyoung Yoon、Jong Hyun Kim、Ina Yoon、Changhoon Kim、Sung-Eun Kim、Yura Koh、Seung Jae Jeong、Jiyoun Lee、Sunghoon Kim、Jeewoo Lee

  DOI：10.1016/j.bmcl.2016.05.011

  日期：2016.7

  A series of leucinol analogs were investigated as leucyl-tRNA synthetase-targeted mTORC1 inhibitors. Among them, compound 5, (S)-4-isobutyloxazolidin-2-one, showed the most potent inhibition on the mTORC1 pathway in a concentration-dependent manner. Compound 5 inhibited downstream phosphorylation of mTORC1 by blocking leucine-sensing ability of LRS, without affecting the catalytic activity of LRS. In addition, compound 5 exhibited cytotoxicity against rapamycin-resistant colon cancer cells, suggesting that LRS has the potential to serve as a novel therapeutic target. (C) 2016 Elsevier Ltd. All rights reserved.