3-[(3-氰基丙基)氨基]丙胺 | 111880-54-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-[(3-氰基丙基)氨基]丙胺
• 英文名称: 3-<(3-cyanopropyl)amino>propylamine
• 英文别名: N3-(3-cyanopropyl)-1,3-diaminopropane；4-[(3-Aminopropyl)amino]butanenitrile；4-(3-aminopropylamino)butanenitrile
• CAS: 111880-54-7
• 化学式: C₇H₁₅N₃
• 分子量: 141.216
• InChiKey: FDWCISPMLWVANL-UHFFFAOYSA-N

物化性质

• 沸点：
  292.0±20.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(3-氰基丙基)氨基]丙胺 在 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N1,N4-双-Boc-亚精胺
  参考文献：
  名称：

  N-酰化的腐胺，亚精胺和亚精胺衍生物的设计，合成和体外抗动素体评估

  摘要：

  对多胺衍生物的构效关系研究导致了17种化合物的合成和抗运动型活性的测定。其中，亚精胺衍生物（化合物13）在体外对利什曼原虫多虫尼阿米虫（IC 50为5.4μM ；选择性指数> 18.5）具有特异性活性，而亚精胺衍生物（化合物28）对布氏锥虫（Trypanosoma brucei gambiense）具有特异性活性（IC 50对1.9μM;选择性指数> 52）。

  DOI：

  10.1016/j.bmcl.2014.11.073
• 作为产物：
  描述：

  1,3-丙二胺 、 4-溴丁腈 反应 2.75h， 以73%的产率得到3-[(3-氰基丙基)氨基]丙胺
  参考文献：
  名称：

  Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds

  摘要：

  描述了一种用于立体选择性地还原连接到融合环基的不饱和烷基酮取代基的方法。在这种方法中，不饱和烷基酮与手性氧化硼腙试剂发生反应。这种反应会将不饱和烷基酮立体选择性地还原为不饱和烷基醇。如果需要，可以进一步还原不饱和烷基醇，以产生饱和烷基醇。融合环基可以是类固醇环基或维生素D类似物的基。根据本发明的工艺可以用于具有烯酮基取代基（例如，22-烯-24-酮基）或炔酮基取代基（例如，22-炔-24-酮基）的类固醇环基，以制备鲨碱或其他有用的氨基类固醇化合物和用于制备氨基类固醇化合物的中间体。

  公开号：

  US06610866B2
• 作为试剂：
  描述：

  3-[(3-氰基丙基)氨基]丙胺 、 potassium (5α,7α,24R)-7-hydroxy-3-ketocholestan-24-yl sulfate 在 3-[(3-氰基丙基)氨基]丙胺 作用下， 生成 [(3R,6R)-6-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-[3-(3-cyanopropylamino)propylamino]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] hydrogen sulfate
  参考文献：
  名称：

  J. Org. Chem. 1998, 63, 8599-8603

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds
  申请人：Magainin Pharmaceuticals, Inc.

  公开号：US06610866B2

  公开（公告）日：2003-08-26

  A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.

  描述了一种用于立体选择性地还原连接到融合环基的不饱和烷基酮取代基的方法。在这种方法中，不饱和烷基酮与手性氧化硼腙试剂发生反应。这种反应会将不饱和烷基酮立体选择性地还原为不饱和烷基醇。如果需要，可以进一步还原不饱和烷基醇，以产生饱和烷基醇。融合环基可以是类固醇环基或维生素D类似物的基。根据本发明的工艺可以用于具有烯酮基取代基（例如，22-烯-24-酮基）或炔酮基取代基（例如，22-炔-24-酮基）的类固醇环基，以制备鲨碱或其他有用的氨基类固醇化合物和用于制备氨基类固醇化合物的中间体。
• Synthesis of Squalamine Utilizing a Readily Accessible Spermidine Equivalent
  作者：Xuehai Zhang、Meenakshi N. Rao、Stephen R. Jones、Bin Shao、Penina Feibush、Melissa McGuigan、Nathan Tzodikov、Binyamin Feibush、Ilya Sharkansky、Brad Snyder、Larry M. Mallis、Ani Sarkahian、Susan Wilder、Joshua E. Turse、William A. Kinney、Hans Jørgen Kjærsgaard、Ronald S. Michalak

  DOI：10.1021/jo981344z

  日期：1998.11.1
• UMEDA, YOSHIHISA;MORIGUCHI, MAKOTO;KURODA, HIROYUKI;NAKAMURA, TERUYA;FUJI+, J. ANTIBIOTICS, 40,(1987) N 9, 1303-1315
  作者：UMEDA, YOSHIHISA、MORIGUCHI, MAKOTO、KURODA, HIROYUKI、NAKAMURA, TERUYA、FUJI+

  DOI：——

  日期：——
• [EN] POLYAMINE TRANSPORT INHIBITORS<br/>[FR] INHIBITEURS DE TRANSPORT DE POLYAMINES
  申请人：UNIV LAVAL

  公开号：WO2000034226A1

  公开（公告）日：2000-06-15

  The application discloses synthetic derivatives of original polyamines in which a carbon atom to the original polyamine comprises an amide group inhibits the e cellular uptake of a natural polyamine by specifically binding a cellular transporter for a natural polyamine . The synthetic derivatives are used to inhibit the activity of a natural polyamine transporter, in the treatment of disorders involving unrestrained cell proliferation and/or differentiation where control of polyamine transport is required When used in combination with a n inhibitor of polyamine synthesis.
• Synthesis of New Alkylaminooxysterols with Potent Cell Differentiating Activities: Identification of Leads for the Treatment of Cancer and Neurodegenerative Diseases
  作者：Philippe de Medina、Michael R. Paillasse、Bruno Payré、Sandrine Silvente-Poirot、Marc Poirot

  DOI：10.1021/jm901063e

  日期：2009.12.10

  We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-alpha-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5 alpha-hydroxyl-6 beta-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5 alpha-Hydroxy-6 beta-[2-(1-H-imidazol-4-yl)ethylamino]cholestan -3 beta-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5 alpha-hydroxyl-6 beta-[3-(4-aminobutylamino)propylamino]cholest-7-en-3 beta-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.