tert-butyl 4-(2-cyanoethylamino)butyl carbamate | 68076-40-4

• 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: tert-butyl 4-(2-cyanoethylamino)butyl carbamate
• 英文别名: tert-Butyl {4-[(2-cyanoethyl)amino]butyl}carbamate；tert-butyl N-[4-(2-cyanoethylamino)butyl]carbamate
• CAS: 68076-40-4
• 化学式: C₁₂H₂₃N₃O₂
• 分子量: 241.334
• InChiKey: YHWSTQMDXGCLEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-cyanoethylamino)butyl carbamate 在 sodium hydroxide 、 氢气 、 镍 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 20.0h， 生成 tert-butyl 4-(3-aminopropylamino)butylcarbamate
  参考文献：
  名称：

  Synthesis of 13C-dilabeled 4-coumaroylspermidines

  摘要：

  Five C-13-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N-1,4-di[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (13b), N-1-[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (17b), N-1,8-di[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (20b), N-4-[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (24b) and N-1,4,8-tri[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (26). The two C-13-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on H-1-H-1 NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the. same way as spermidine does, whereas 24b and 26 do not-show any NOE effects with the tRNA protons. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01014-x
• 作为产物：
  描述：

  2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.5h， 生成 tert-butyl 4-(2-cyanoethylamino)butyl carbamate
  参考文献：
  名称：

  [EN] STEROID-HORMONE CONJUGATES WITH POLYAMINES AND THEIR THERAPEUTIC USE AS ANTI-CANCER AND ANGIOSTATIC AGENTS
  [FR] CONJUGUES D'HORMONES STEROIDES AVEC POLYAMINES ET UTILISATION THERAPEUTIQUE DE CEUX-CI EN TANT QU'AGENTS ANTICANCEREUX ET ANGIOSTATIQUES

  摘要：

  化合物的化学式（I）：{其中：R1和R2中的一个代表化学式（II）的基团：-NH-(CH2)N-NH-[(CH2)m-NH]x-[(CH2)p-NH]y（II）[其中n、m和p分别代表2至6之间的数字；x和y分别代表零或1至2之间的数字]；另一个R1和R2代表氢、氧、羟基、Cl - C6烷酰基团或上述化学式（II）的基团；R3和R4分别代表氧、羟基、巯基、氢、卤素、烷氧基或芳基氧基；R5代表氢或甲基或不存在；虚线表示单键或双键；虚圆表示相邻碳原子对之间的双键数量为零、一、二或三}; 其酯类化合物对于治疗或预防肿瘤和/或糖尿病性视网膜病变是有用的。

  公开号：

  WO2005116050A1

文献信息

• Efficient Synthesis of Orthogonally Protected Spermidine and Norspermidine Derivatives
  作者：Ryszard Andruszkiewicz、Michał Radowski、Zbigniew Czajgucki

  DOI：10.1081/scc-200054211

  日期：2005.4.1

  Abstract Several orthogonally protected spermidine and norspermidine derivatives have been synthesized via cyanoethylation of monoprotected 1,4‐butanediamine (putrescine) or 1,3‐propanediamine followed by protection of their secondary amino groups and final reduction of the nitriles with lithium aluminum hydride in etheral solution at 0°C, thus affording protected norspermidine or spermidine that may

  摘要 通过单保护的 1,4-丁二胺（腐胺）或 1,3-丙二胺的氰乙基化，然后保护它们的仲氨基，最后在醚溶液中用氢化铝锂还原腈类，合成了几种正交保护的亚精胺和去甲精胺衍生物。在0°C，从而提供可用于合成多胺酰胺或可进一步官能化的受保护的去甲精胺或亚精胺。
• [EN] FUNCTIONALIZED LINEAR LIGANDS AND COMPLEXES THEREOF<br/>[FR] LIGANDS LINÉAIRES FONCTIONNALISÉS ET COMPLEXES DE CEUX-CI
  申请人：LUMIPHORE INC

  公开号：WO2016106241A1

  公开（公告）日：2016-06-30

  The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

  这项发明涉及可用于治疗和诊断应用的化合物和配合物。
• 用于苦柯胺B质量控制中的参比化合物
  申请人：天津红日药业股份有限公司

  公开号：CN105330563B

  公开（公告）日：2018-12-07

  本发明涉及用于苦柯胺B质量控制中的四种参比化合物，及其制备方法，以及用此三种参比化合物控制苦柯胺B质量的质量控制方法。
• Anchoring Cationic Amphiphiles for Nucleotide Delivery Significance of DNA Release from Cationic Liposomes for Transfection
  作者：Naohide Hirashima、Kazuhiro Minatani、Yoshifumi Hattori、Tomohiko Ohwada、Mamoru Nakanishi

  DOI：10.1248/bpb.30.1117

  日期：——

  We have designed and synthesized lithocholic acid-based cationic amphiphile molecules as components of cationic liposomes for gene transfection (lipofection). To study the relationship between the molecular structures of those amphiphilic molecules, particularly the extended hydrophobic appendant (anchor) at the 3-hydroxyl group, and transfection efficiency, we synthesized several lithocholic and isolithocholic acid derivatives, and examined their transfection efficiency. We also compared the physico-chemical properties of cationic liposomes prepared from these derivatives. We found that isolithocholic acid derivatives exhibit higher transfection efficiency than the corresponding lithocholic acid derivatives. This result indicates that the orientation and extension of hydrophobic regions influence the gene transfection process. Isolithocholic acid derivatives showed a high ability to encapsulate DNA in a compact liposome–DNA complex and to protect it from enzymatic degradation. Isolithocholic acid derivatives also facilitated the release of DNA from the liposome–DNA complex, which is a crucial step for DNA entry into the nucleus. Our results show that the transfection efficiency is directly influenced by the ability of the liposome complex to release DNA, rather than by the DNA-encapsulating ability. Molecular modeling revealed that isolithocholic acid derivatives take relatively extended conformations, while the lithocholic acid derivatives take folded structures. Thus, the efficiency of release of DNA from cationic liposomes in the cytoplasm, which contributes to high transfection efficiency, appears to be dependent upon the molecular shape of the cationic amphiphiles.

  我们设计并合成了以石胆酸为基础的阳离子两性分子，作为阳离子脂质体中基因转染（脂质转染）的组成部分。为了研究这些两性分子分子结构之间的关系，尤其是3-羟基基团处的延伸疏水附加物（锚）与转染效率之间的关系，我们合成了几种石胆酸和异石胆酸的衍生物，并检查了它们的转染效率。我们还比较了由这些衍生物制备的阳离子脂质体的物理化学性质。我们发现，异石胆酸衍生物的转染效率高于相应的石胆酸衍生物。这一结果表明，疏水区域的朝向和延伸影响了基因转染过程。异石胆酸衍生物展现出高能力在紧凑的脂质体–DNA复合物中包裹DNA，并保护其免受酶的降解。异石胆酸衍生物还促进了DNA从脂质体–DNA复合物的释放，这对于DNA进入细胞核是一个关键步骤。我们的结果表明，转染效率直接受脂质体复合物释放DNA能力的影响，而不是DNA包裹能力的影响。分子建模显示，异石胆酸衍生物呈现出相对延伸的构象，而石胆酸衍生物则呈现折叠的结构。因此，高转染效率所需的DNA从细胞质中阳离子脂质体释放的效率似乎依赖于阳离子两性分子的分子形状。
• SALTS OF KUKOAMINE B, PREPARATION METHOD AND USE THEREOF
  申请人：Zheng Jiang

  公开号：US20130289112A1

  公开（公告）日：2013-10-31

  Salts of kukoamine B, their preparation method and their pharmaceutical use in preparation of drugs for preventing and treating sepsis. Experiments indicate that salts of kukoamine B have a good effect on antagonizing the key factors inducing sepsis, and can be used in the preparation of drugs for preventing and treating sepsis. Under the current circumstances of the lack of effective measures for the treatment of sepsis in clinical practice, the medicinal formulations, which comprise the salts of kukoamine B, pharmaceutically acceptable carrier and/or diluent, provide a new approach for the prevention and treatment of sepsis.

  库酰胺B盐的制备方法及其在制备用于预防和治疗败血症的药物中的药用。实验表明，库酰胺B盐对抗败血症诱导的关键因素有良好的效果，并可用于制备用于预防和治疗败血症的药物。在当前临床实践中缺乏有效治疗败血症措施的情况下，包括库酰胺B盐、药用载体和/或稀释剂的药物配方为预防和治疗败血症提供了新的途径。