(+/-)-(cis)-N,N'-bis(tert-butyloxycarbonyl)-1,2-cyclopropanediamine | 68979-49-7

• 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: (+/-)-(cis)-N,N'-bis(tert-butyloxycarbonyl)-1,2-cyclopropanediamine
• 英文别名: tert-butyl N-[(1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropyl]carbamate
• CAS: 68979-49-7
• 化学式: C₁₃H₂₄N₂O₄
• 分子量: 272.345
• InChiKey: XEFAFUIKGFRZRK-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(cis)-N,N'-bis(tert-butyloxycarbonyl)-1,2-cyclopropanediamine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以63%的产率得到(+/-)-(cis)-N-tert-butyloxycarbonyl-1,2-cyclopropanediamine
  参考文献：
  名称：

  Benzamides derived from 1,2-diaminocyclopropane as novel ligands for human D 2 and D 3 dopamine receptors

  摘要：

  Benzamides (3a-f) derived from 4-amino-5-chloro-2-methoxybenzoic acid and either cis or trans 1,2-diamino cyclopropane were synthesised and were evaluated in binding assays employing, bovine striatal D-2 receptors, recombinant human hD(2) and hD(3) receptors expressed in CHO cells and rat, cortical 5-HT3 and striatal 5-HT4 receptors. The cis and trans isomers of the derivatives were isolated and characterised. The results demonstrated the superiority of the cis conformers over the trans conformers in dopamine receptor binding assays (K-i hD(2) = 13.4 and 6.9 nM and K-i hD(3) = 17.7 and 4.5 nM for the cis-3b and cis-3f compounds, respectively; K-i hD(2) = 816 and >1000 nM and K-i hD(3) = 469 and >1000 nM for the corresponding trans-3b and trans-3f compounds respectively). The cis compounds are folded: the benzamide group and the basic nitrogen atom were in a syn relationship. Compound 3f can be superimposed with a conformation of the tropane derivative, BRL 25594, having the benzyl group in an axial position to give a suitable fit, indicating that both compounds may have a common binding site in the dopamine receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00281-3
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 cis-cyclopropane-1,2-diamine dihydrochloride 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以77%的产率得到(+/-)-(cis)-N,N'-bis(tert-butyloxycarbonyl)-1,2-cyclopropanediamine
  参考文献：
  名称：

  Benzamides derived from 1,2-diaminocyclopropane as novel ligands for human D 2 and D 3 dopamine receptors

  摘要：

  Benzamides (3a-f) derived from 4-amino-5-chloro-2-methoxybenzoic acid and either cis or trans 1,2-diamino cyclopropane were synthesised and were evaluated in binding assays employing, bovine striatal D-2 receptors, recombinant human hD(2) and hD(3) receptors expressed in CHO cells and rat, cortical 5-HT3 and striatal 5-HT4 receptors. The cis and trans isomers of the derivatives were isolated and characterised. The results demonstrated the superiority of the cis conformers over the trans conformers in dopamine receptor binding assays (K-i hD(2) = 13.4 and 6.9 nM and K-i hD(3) = 17.7 and 4.5 nM for the cis-3b and cis-3f compounds, respectively; K-i hD(2) = 816 and >1000 nM and K-i hD(3) = 469 and >1000 nM for the corresponding trans-3b and trans-3f compounds respectively). The cis compounds are folded: the benzamide group and the basic nitrogen atom were in a syn relationship. Compound 3f can be superimposed with a conformation of the tropane derivative, BRL 25594, having the benzyl group in an axial position to give a suitable fit, indicating that both compounds may have a common binding site in the dopamine receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00281-3

文献信息

• Substituierte Piperidino-Dihydrothienopyrimidine
  申请人：BOEHRINGER INGELHEIM INTERNATIONAL GMBH

  公开号：EP2610258A1

  公开（公告）日：2013-07-03

  Die Erfindung betrifft neue Piperidino-Dihydrothienopyrimidine der Formel 1, sowie pharmakologisch verträgliche Salze davon, worin X SO oder SO2, vorzugsweise jedoch SO, ist und worin R1, R2, R3 und R4 die in Anspruch 1 genannten Bedeutungen haben kann, sowie pharmazeutische Zusammensetzungen, die diese Verbindungen beinhalten. Diese neuen Piperidino-Dihydrothienopyrimidine sind geeignet zur Behandlung von Atemwegs- oder gastrointestinalen Beschwerden oder Erkrankungen, entzündliche Erkrankungen der Gelenke, der Haut oder der Augen, Erkrankungen des periphären oder zentralen Nervensystems oder Krebserkrankungen.

  本发明涉及式 1 的新型哌啶二氢噻吩嘧啶及其药理上可接受的盐类、 其中X为SO或SO2，但优选SO，R1、R2、R3和R4可具有权利要求1中给出的含义，以及包含这些化合物的药物组合物。 这些新的哌啶二氢噻吩嘧啶类化合物适用于治疗呼吸道或胃肠道不适或疾病，关节、皮肤或眼睛的炎症性疾病，外周或中枢神经系统疾病或癌症。
• US8754073B2
  申请人：——

  公开号：US8754073B2

  公开（公告）日：2014-06-17
• K-RAS MUTANT PROTEIN INHIBITORS
  申请人：[en]JACOBIO PHARMACEUTICALS CO., LTD.

  公开号：WO2024041621A1

  公开（公告）日：2024-02-29

  The invention provides K-Ras mutant protein inhibitors of formula (Ⅰ), a composition containing the same and the use thereof.
• Benzamides derived from 1,2-diaminocyclopropane as novel ligands for human D 2 and D 3 dopamine receptors
  作者：Donglai Yang、Slaheddine Kefi、Valérie Audinot、Mark-J. Millan、Michel Langlois

  DOI：10.1016/s0968-0896(99)00281-3

  日期：2000.2

  Benzamides (3a-f) derived from 4-amino-5-chloro-2-methoxybenzoic acid and either cis or trans 1,2-diamino cyclopropane were synthesised and were evaluated in binding assays employing, bovine striatal D-2 receptors, recombinant human hD(2) and hD(3) receptors expressed in CHO cells and rat, cortical 5-HT3 and striatal 5-HT4 receptors. The cis and trans isomers of the derivatives were isolated and characterised. The results demonstrated the superiority of the cis conformers over the trans conformers in dopamine receptor binding assays (K-i hD(2) = 13.4 and 6.9 nM and K-i hD(3) = 17.7 and 4.5 nM for the cis-3b and cis-3f compounds, respectively; K-i hD(2) = 816 and >1000 nM and K-i hD(3) = 469 and >1000 nM for the corresponding trans-3b and trans-3f compounds respectively). The cis compounds are folded: the benzamide group and the basic nitrogen atom were in a syn relationship. Compound 3f can be superimposed with a conformation of the tropane derivative, BRL 25594, having the benzyl group in an axial position to give a suitable fit, indicating that both compounds may have a common binding site in the dopamine receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.