O,O'-1,6-hexanediylbishydroxylamine dihydrochloride | 34960-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O,O'-1,6-hexanediylbishydroxylamine dihydrochloride
• 英文别名: 1,6-bis-aminooxy-hexane; dihydrochloride；1,6-Bis-aminooxy-hexan; Dihydrochlorid
• CAS: 34960-06-0
• 化学式: C₆H₁₆N₂O₂*2ClH
• 分子量: 221.127
• InChiKey: PYURRXYWYMXPCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  11.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O,O'-1,6-hexanediylbishydroxylamine dihydrochloride 、 N-[2-(dimethylamino)ethyl]-11-oxoindeno[1,2-b]quinoline-6-carboxamide 在 盐酸 作用下， 反应 3.0h， 以84%的产率得到11,11'-[(O,O'-hexane-1,6-diyl)bisisonitroso]bis-[N-[2-(dimethylamino)ethyl]-11H-indeno[1,2-b]quinoline-6-carboxamide]
  参考文献：
  名称：

  Synthesis and antitumor activity of some indeno[1,2- b ]quinoline-based bis carboxamides

  摘要：

  A series of bis(11-oxo-1 1H-indeno[1,2-b]quinoline-6-carboxamides) linked through the B-carboxamides were prepared by coupling the requisite acid imidazolides with Various diamines. Compounds with mono-cationic linker chains were more potent cytotoxins than the corresponding monomer in a panel of rodent and human cell lines: while those with the dicationic linker chains (CH2)(2)NR(CH2)(2)NR(CH2)(2) and (CH2)(2)NR(CH2)(3)NR(CH2)(2) showed extraordinarily high potencies (for example, IC(50)s of 0.18-1.4 nM against human Jurkat leukemia; up to 1000-fold more potent than the parent monomer). As seen previously in the monomeric series, small, lipophilic 4-substituents significantly increased potency in cell culture. The dimeric compounds were all slightly to significantly more potent in the mutant JL(A) and JL(D) cell lines that under-express topo II, suggesting that this enzyme is not their primary target. An Il-imino-linked dimer was much less active, and an asymmetric indeno[1,2-b]quinoline-6-carboxamide/naphthalimide dimer was less active than the comparable symmetric bis(indeno[1,2-b]quinoline-6-carboxamide). Selected analogues were active against sub-cutaneously implanted colon 38 tumors in mice? giving growth delays comparable to that of the clinical topo I inhibitor irinotecan at up to 10-fold lower doses. These compounds form an interesting new class of putative topo I inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00039-0
• 作为产物：
  描述：

  diethyl N',N''-(hexane-1,6-diylbis(oxy))diacetimidate 在 盐酸 、 水 作用下， 以 异丙醇 为溶剂， 以93%的产率得到O,O'-1,6-hexanediylbishydroxylamine dihydrochloride
  参考文献：
  名称：

  Novel convenient synthesis of biologically active esters of hydroxylamine

  摘要：

  Alkylation of ethyl N-hydroxyacetimidate with readily available methanesulfonates of functionally substituted alcohols and subsequent deprotection of aminooxy group is a novel and convenient method to prepare functionally substituted esters of hydroxylamine with high overall yield. This approach is a good alternative to well-known reaction of N-hydroxyphthalimide with alcohols under the Mitsunobu conditions. The properties of ethoxyethylidene protection of aminooxy group on the contrary to that of N-alkoxyphthalimide group allow to perform a wide spectra of the transformations in the radical of N-protected hydroxylamine derivatives. This is essential for synthetic strategies consisting in the introduction of N-protected aminooxy group at one of the first steps of synthesis and subsequent transformations of the radical.The inhibitory effect of one of the newly synthesized compound, 1-guanidinooxy-3-aminopropane (GAPA), was compared with that of well-known inhibitors of ornithine decarboxylase namely, alpha-difluoromethylornithine (DFMO) and 1-aminooxy-3-aminopropane (APA) on Leishmania donovani, a protozoan parasite that causes visceral leishmaniasis. GAPA, on the contrary with APA and DFMO, in micromolar concentrations, inhibited the growth of both amastigotes and promastigotes of sodium antimony gluconate-resistant forms of L. donovani.

  DOI：

  10.1007/s00726-009-0410-0