1,12-bis(1-deoxy-D-glucitol-1-ylamino)dodecane | 171745-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,12-bis(1-deoxy-D-glucitol-1-ylamino)dodecane
• 英文别名: (2R,3R,4R,5S)-6-[12-[[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]dodecylamino]hexane-1,2,3,4,5-pentol
• CAS: 171745-72-5
• 化学式: C₂₄H₅₂N₂O₁₀
• 分子量: 528.684
• InChiKey: VYNHKWQLJWBFHK-BPIZVXQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  36
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  226
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (Z)-十八碳-9-烯醛 、 1,12-bis(1-deoxy-D-glucitol-1-ylamino)dodecane 在 溶剂黄146 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 68.0h， 以81%的产率得到
  参考文献：
  名称：

  Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer

  摘要：

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.023
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 platinum(IV) oxide 氢气 作用下， 以 水 为溶剂， 22.5~60.0 ℃ 、413.68 kPa 条件下， 生成 1,12-bis(1-deoxy-D-glucitol-1-ylamino)dodecane
  参考文献：
  名称：

  In Vivo Cadmium Mobilization by Three Novel Bis(carbodithioates)

  摘要：

  Four novel cadmium-chelating agents N,N'di(D-glucosyl)alkanediamine-N,N'-bis(carbodithioates) 4a-e were prepared as disodium salts of the general formula (CH2)(n)[N(CS2Na)-CH2(CHOH)(4)CH2OH](2), where n = 7, 8, 10, and 12. They were synthesized by the reductive coupling of 2 mol of alpha-D-(+)-glucose (1) with 1 mol of the corresponding alkanediamines 2a-e followed by reaction with CS2 in a basic medium. The elemental analyses of the Cd complexes 5a, b, d, and e prepared revealed that these bis(carbodithioates) form 1:1 complexes with Cd2+. The in vivo cadmium-mobilizing efficacy of three of the new chelators (4a, b, and d) was determined in rats pretreated ip with CdCl2 . H2O containing 2 mu Ci of Cd-109 (74 kBq), and comparable data were obtained on a previously reported member of this series (4c, n = 9), and with BGDTC (sodium N-benzyl-D-glucamine-N-carbodithioate, 6), all given once at 1.0 mmol/kg ip. The compound with n = 12 (4e, C12G2DTC) proved to be too toxic in the preliminary study and was not evaluated further. A single injection of the 4a, b, and d caused a reduction in Cd levels of the whole body to ca. 50% and liver to ca. 12% of control levels. Comparable experimental data on BGDTC resulted in a reduction of whole-body cadmium to only 78% of the control levels and a reduction in liver cadmium to only 56% of control. After one and six injections at the same dosage, the new chelators (4a, b, and d) and C9G2DTC (4c, n = 9) significantly surpassed BGDTC for whole-body and liver Cd depletion but caused only a very modest depletion of renal Cd. While these compounds were designed to allow the two dithiocarbamate groups to coordinate to the same Cd2+ in vivo, the data do not prove that the two > NCS2Na groups bind to the same cadmium ion in vivo. The very rapid reduction in liver cadmium levels following only a single injection indicates that these -2 anions rapidly gain access to intracellular hepatic sites by some transport system.

  DOI：

  10.1021/tx950123a

文献信息

• Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer
  作者：Anno Wagenaar、Jan B.F.N. Engberts

  DOI：10.1016/j.tet.2007.08.023

  日期：2007.10

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.
• <i>In Vivo</i> Cadmium Mobilization by Three Novel Bis(carbodithioates)
  作者：Pramod K. Singh、Mark M. Jones、Krista Kostial、Maja Blanuša、Martina Piasek

  DOI：10.1021/tx950123a

  日期：1996.1.1

  Four novel cadmium-chelating agents N,N'di(D-glucosyl)alkanediamine-N,N'-bis(carbodithioates) 4a-e were prepared as disodium salts of the general formula (CH2)(n)[N(CS2Na)-CH2(CHOH)(4)CH2OH](2), where n = 7, 8, 10, and 12. They were synthesized by the reductive coupling of 2 mol of alpha-D-(+)-glucose (1) with 1 mol of the corresponding alkanediamines 2a-e followed by reaction with CS2 in a basic medium. The elemental analyses of the Cd complexes 5a, b, d, and e prepared revealed that these bis(carbodithioates) form 1:1 complexes with Cd2+. The in vivo cadmium-mobilizing efficacy of three of the new chelators (4a, b, and d) was determined in rats pretreated ip with CdCl2 . H2O containing 2 mu Ci of Cd-109 (74 kBq), and comparable data were obtained on a previously reported member of this series (4c, n = 9), and with BGDTC (sodium N-benzyl-D-glucamine-N-carbodithioate, 6), all given once at 1.0 mmol/kg ip. The compound with n = 12 (4e, C12G2DTC) proved to be too toxic in the preliminary study and was not evaluated further. A single injection of the 4a, b, and d caused a reduction in Cd levels of the whole body to ca. 50% and liver to ca. 12% of control levels. Comparable experimental data on BGDTC resulted in a reduction of whole-body cadmium to only 78% of the control levels and a reduction in liver cadmium to only 56% of control. After one and six injections at the same dosage, the new chelators (4a, b, and d) and C9G2DTC (4c, n = 9) significantly surpassed BGDTC for whole-body and liver Cd depletion but caused only a very modest depletion of renal Cd. While these compounds were designed to allow the two dithiocarbamate groups to coordinate to the same Cd2+ in vivo, the data do not prove that the two > NCS2Na groups bind to the same cadmium ion in vivo. The very rapid reduction in liver cadmium levels following only a single injection indicates that these -2 anions rapidly gain access to intracellular hepatic sites by some transport system.