N-methylpiperazinium thiocyanate | 1278588-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-methylpiperazinium thiocyanate
• 英文别名: 1-Methylpiperazine;thiocyanic acid
• CAS: 1278588-63-8
• 化学式: CHNS*C₅H₁₂N₂
• 分子量: 159.255
• InChiKey: WPASOZFIBCYNCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methylpiperazinium thiocyanate 在 盐酸羟胺 、 氢气 、 sodium ethanolate 、 三乙胺 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0~160.0 ℃ 、344.75 kPa 条件下， 反应 128.0h， 生成 (2SR,6RS,7RS)-(+/-)-2-diethylamino-N-(4-(4-methylpiperazin-1-yl)-6,7-diphenylbicyclo[2.2.2]octan-2-yl)acetamide
  参考文献：
  名称：

  Antiprotozoal activity of bicyclic diamines with a N-methylpiperazinyl group at the bridgehead atom

  摘要：

  omega-Aminoacyl and -alkyl derivatives of 4-(4-methylpiperazin-1-yl)bicyclo[2.2.2]octan-2-amines and of 5-(4-methylpiperazin-1-yl)-2-azabicyclo[3.2.2]nonanes were prepared and their activities were examined in vitro against the multiresistant K-1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). Some of the newly synthesized compounds showed very promising antiprotozoal activity and selectivity. A few of the allcylamino-2-azabicyclo[3.2.2]nonanes exhibited high antiplasmodial activity, whereas a single bicyclo[2.2.2]octane derivative was the most potent antitrypanosomal compound. The results of the newly synthesized compounds were compared with the activities of already synthesized compounds and of drugs in use. Structure-activity relationships were discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.059

文献信息

• Novel antimalarial 3-azabicyclo[3.2.2]nonane derivatives
  申请人：University of Graz

  公开号：EP2301627A1

  公开（公告）日：2011-03-30

  The present invention relates to novel 3-azabicyclo[3.2.2]nonane derivatives of the general formula (I) or a pharmaceutically acceptable salt thereof wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are as defined in the specification. The novel 3-azabicyclo[3.2.2]nonane derivatives are particularly useful for treatment and prevention of malaria and trypanosomiasis.

  本发明涉及一般式(I)的新型3-氮杂双环[3.2.2]壬烷衍生物 或其药学上可接受的盐 其中R1、R2、R3、R4、R5、R6、R7、R8、R9和R10如规范中所定义。这些新型3-氮杂双环[3.2.2]壬烷衍生物特别适用于治疗和预防疟疾和锥虫病。
• New N-methylpiperazinyl derivatives of bicyclic antiprotozoal compounds
  作者：Johanna Faist、Werner Seebacher、Robert Saf、Reto Brun、Marcel Kaiser、Robert Weis

  DOI：10.1016/j.ejmech.2011.11.022

  日期：2012.1

  bicyclic compounds or as terminal group of their aminoacyl and aminoalkyl side chains. The new compounds were tested in vitro for their activities against the multidrug-resistant K1 strain of Plasmodium falciparum and Trypanosoma brucei rhodesiense (STIB 900). The results were compared to those of formerly prepared analogues and of drugs in use. A couple of bicyclo-octyl ω-(4-piperazin-1-yl)alkanoates

  4-甲基哌嗪基作为取代基插入双环化合物的桥头或作为其氨基酰基和氨基烷基侧链的末端基团。在体外测试了这些新化合物对恶性疟原虫和布鲁氏罗得氏锥虫（STIB 900）的多重耐药性K 1菌株的活性。将结果与先前制备的类似物和使用中的药物进行比较。一对夫妇二环辛基ω-（4-哌嗪-1-基）链烷酸酯的表现出较高的抗锥体虫（IC 50  ≤0.087μM）和抗疟原虫活性（IC 50  ≤0.06μM）。活性最高的ω-（4-甲基哌嗪-1-基）烷基-2-氮杂双环壬烷具有较高的抗血浆活性（IC 50≤0.023μM  ）和选择性（SI = IC 50（Cytotox。）/ IC 50（恶性疟原虫）= 2188）比抗疟疾药物氯喹（IC 50  = 0.15μM，SI = 1257）。
• New derivatives of bicyclic diamines with antiprotozoal activity
  作者：Johanna Faist、Werner Seebacher、Robert Saf、Reto Brun、Marcel Kaiser、Robert Weis

  DOI：10.1007/s00706-015-1592-7

  日期：2016.2

  Abstractω-Aminoacyl and -alkyl derivatives of 4-(dialkylamino)bicyclo[2.2.2]octan-2-amines and of 5-(dialkylamino)-2-azabicyclo[3.2.2]nonanes were prepared and their activities were examined in vitro against the multiresistant K1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). The results of the biological tests of the newly synthesized compounds were compared

  摘要制备了4-（二烷基氨基）双环[2.2.2]辛-2-胺和5-（二烷基氨基）-2-氮杂双环[3.2.2]壬烷的ω-氨基酰基和-烷基衍生物，并在体外对其活性进行了研究。对抗恶性疟原虫的多抗性K 1菌株和布鲁氏罗得氏锥虫（STIB 900）。将新合成的化合物的生物学测试结果与已经合成的化合物和所用药物的活性进行了比较。许多新合成的化合物显示出有希望的抗原生动物特性和选择性，其中一些具有比氯喹更高的抗疟原虫活性。讨论了构效关系。 图形概要
• US4064244A
  申请人：——

  公开号：US4064244A

  公开（公告）日：1977-12-20
• [EN] NOVEL ANTIMALARIAL 3-AZABICYCLO[3.2.2]NONANE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS ANTIPALUDIQUES DE 3-AZABICYCLO[3.2.2]NONANE
  申请人：UNIV GRAZ

  公开号：WO2011035355A1

  公开（公告）日：2011-03-31

  The present invention relates to novel 3-azabicyclo[3.2.2]nonane derivatives of the general formula (I) or a pharmaceutically acceptable salt thereof wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are as defined in the specification. The novel 3-azabicyclo[3.2.2]nonane derivatives are particularly useful for treatment and prevention of malaria and trypanosomiasis.