N-BOC-4-硝基苯乙胺 | 144226-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-BOC-4-硝基苯乙胺
• 中文别名: N-(2-(4-硝基苯基)乙基)氨基甲酸叔丁酯；[2-(4-硝基苯基)乙基]氨基甲酸叔丁酯
• 英文名称: tert-butyl (4-nitrophenethyl)carbamate
• 英文别名: (tert-butoxy)-N-[2-(4-nitrophenyl)-ethyl]-carboxamide；Tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate
• CAS: 144226-16-4
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: GDPYNCZCYJBYIN-UHFFFAOYSA-N

物化性质

• 沸点：
  422.3±28.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  N-BOC-4-硝基苯乙胺 在 palladium on activated charcoal 盐酸 、 3 A molecular sieve 、 氢气 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 N-<4-(2-Amino-ethyl)-phenyl>-diethanolamin
  参考文献：
  名称：

  Synthesis and evaluation of novel spermidine derivatives as targeted cancer chemotherapeutic agents

  摘要：

  The utility of the spermidine moiety as the homing device for the selective delivery of chemotherapeutic and diagnostic agents into cancer cells was explored. Two spermidine analogs containing a cytotoxic agent were synthesized, N-[3,4-bis(benzyloxy)phenethyl]-N(alpha)-(3-amino-propyl)-L-ornithinamide trihydrochloride, 1a and N-[4-[bis(2-chloroethyl)amino]phenethyl]-N(alpha)-(3-aminopropyl)-L-ornithinamide tetrahydrochloride, lb. These compounds were prepared from the fully protected spermidine molecule with a carboxyl group side chain, 8. The ability of the polyamine cytotoxic agents to inhibit B16-BL6 melanoma cell growth in culture was examined. The effects of pretreatment with DFMO on the activity of the synthesized compounds was also studied. The IC50 values of compounds la and lb were on the same order of magnitude as the control compounds, N-acetyldopamine and chlorambucil, respectively. The inhibitory activities of compounds la and lb were not enhanced by pretreatment with DFMO, suggesting that depletion of intracellular polyamines did not enhance the activity of these compounds.

  DOI：

  10.1021/jm00101a002
• 作为产物：
  描述：

  N-(叔丁氧羰基)乙醇胺 在 咪唑 、 三甲基氯硅烷 、 碘 、 1,2-二溴乙烷 、 三苯基膦 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.25h， 生成 N-BOC-4-硝基苯乙胺
  参考文献：
  名称：

  Efficient synthesis of protected β-phenylethylamines, enantiomerically pure protected β-phenyl-α-benzylethylamines and β-phenyl-α-isopropylethylamines using organozinc chemistry

  摘要：

  β-氨基烷基锌试剂9a、10和11已经使用DMF作为溶剂高效制备。使用钯催化剂在温和便捷的条件下将这些试剂与取代苯基碘化物偶联，可以获得保护的β-苯乙胺6，产率为72–80%（三个例子）；获得对映体纯的保护β-苯-α-苄基乙胺7，产率为53–61%（四个例子）；以及保护的β-苯-α-异丙基乙胺8，产率为53–79%（四个例子）。

  DOI：

  10.1039/a907629h

文献信息

• [EN] COMPOUNDS AND METHODS USEFUL FOR TREATMENT OF DISEASES MEDIATED BY HIF-1<br/>[FR] COMPOSÉS ET MÉTHODES UTILES DANS LE TRAITEMENT DE MALADIES INDUITES PAR HIF-1
  申请人：ONCOTHYREON INC

  公开号：WO2012058325A1

  公开（公告）日：2012-05-03

  Provided herein are compounds that are useful in treatment of diseases mediated by HIF-1.

  这里提供了一些在治疗由HIF-1介导的疾病中有用的化合物。
• Substituted arylsulfides, arylsulfoxides and arylsulfones as beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020040023A1

  公开（公告）日：2002-04-04

  This invention provides compounds of Formula I having the structure 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y, Z, m, n, 2 and are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type 11 diabetes.

  本发明提供了具有以下结构式的I型化合物： 1 其中R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y, Z, m, n, 2 以及前述定义的 pharmaceutically acceptable salt，它们在治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠疾病、神经源性炎症、青光眼、眼压升高和频繁排尿方面非常有用；它们在治疗或抑制2型糖尿病方面特别有用。
• Substituted alkylamine derivatives and methods of use
  申请人：Amgen Inc.

  公开号：US20030225106A1

  公开（公告）日：2003-12-04

  Selected amines are effective for prophylaxis and treatment of diseases, such as angiogenesis mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  选定的胺对预防治疗疾病有效，如血管生成介导的疾病。本发明包括新的化合物、类似物、前药和药用可接受的盐，药物组合物和预防治疗疾病和其他疾病或状况的方法，包括癌症等。本发明还涉及制造这类化合物的过程以及在此类过程中有用的中间体。
• Heterocyclic beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020028832A1

  公开（公告）日：2002-03-07

  This invention provides compounds of Formula I having the structure 1 U, V, W, X, and Y are as defined hereinbefore, or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, glaucoma, ocular hypertension and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  这项发明提供了具有结构式I的化合物 1 其中U、V、W、X和Y如前文所定义， 或其药学上可接受的盐，用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢紊乱（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道疾病、神经炎症、青光眼、眼压增高和频繁排尿；特别适用于治疗或抑制2型糖尿病。
• [EN] AMINOETHYLAROMATIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR<br/>[FR] COMPOSES AMINOETHYLAROMATIQUES PERMETTANT DE TRAITER DES TROUBLES REPONDANT A UNE MODULATION DU RECEPTEUR D3 DE LA DOPAMINE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2006040179A1

  公开（公告）日：2006-04-20

  The present invention relates to aromatic compounds of the formula (I) wherein Ar is phenyl or an aromatic 5- or 6-membered C-bound heteroaromatic radical, wherein Ar may carry 1 radical Ra and wherein Ar may also carry 1 or 2 radicals Rb; X is N or CH; E is CR6R7 or NR3; R1 is C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated Cl-C4­-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3-C4­-alkenyl, formyl or C1-C3-alkylcarbonyl; R1a is H, C1-C4-alkyl, C3-C4-cycloalkyl, C3-C4-cycloalkylmethyl, C3-C4-alkenyl, fluorinated C1-­C4-alkyl, fluorinated C3-C4-cycloalkyl, fluorinated C3-C4-cycloalkylmethyl, fluorinated C3­-C4-alkenyl, or R1a and R2 together are (CH2)n with n being 2, 3 or 4, or R1a and R2a together are (CH2)n with n being 2, 3 or 4; R2 and R2a are independently of each other H, C1-C4-alkyl or fluorinated C1-C4-alkyl or R2a and R2 together are (CH2)m with m being 1, 2, 3, 4 or 5; R3 is H or C1-C4-alkyl; R6, R7 independently of each other are selected from H, fluorine, C1-C4-alkyl and fluorinated C1-C4-alkyl or together form a moiety (CH2)p with p being 2, 3, 4 or 5; and the physiologically tolerated acid addition salts thereof. The invention also relates to the use of a compound of the formula (I) or a pharmaceutically acceptable salt thereof for preparing a pharmaceutical composition for the treatment of a medical disorder susceptible to treatment with a dopamine D3 receptor ligand.

  本发明涉及公式（I）的芳香族化合物，其中Ar为苯基或芳香族5-或6-成员C-键合杂环基，其中Ar可能携带1个基团Ra，Ar也可能携带1个或2个基团Rb；X为N或CH；E为CR6R7或NR3；R1为C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的Cl-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，甲酰基或C1-C3-烷基羰基；R1a为H，C1-C4-烷基，C3-C4-环烷基，C3-C4-环烷基甲基，C3-C4-烯基，氟代的C1-C4-烷基，氟代的C3-C4-环烷基，氟代的C3-C4-环烷基甲基，氟代的C3-C4-烯基，或R1a和R2一起为（CH2）n，其中n为2、3或4，或R1a和R2a一起为（CH2）n，其中n为2、3或4；R2和R2a彼此独立为H，C1-C4-烷基或氟代的C1-C4-烷基，或R2a和R2一起为（CH2）m，其中m为1、2、3、4或5；R3为H或C1-C4-烷基；R6、R7彼此独立地选自H、氟、C1-C4-烷基和氟代的C1-C4-烷基，或一起形成一个(CH2)p的基团，其中p为2、3、4或5；以及其生理耐受的酸盐。该发明还涉及使用公式（I）的化合物或其药学上可接受的盐来制备用于治疗可用多巴胺D3受体配体治疗的医疗疾病的药物组合物。