14-Methylsulfonyloxytetradec-9-ynyl methanesulfonate | 1026489-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 14-Methylsulfonyloxytetradec-9-ynyl methanesulfonate
• CAS: 1026489-03-1
• 化学式: C₁₆H₃₀O₆S₂
• 分子量: 382.543
• InChiKey: DDVJZPYSKDEURX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  14-Methylsulfonyloxytetradec-9-ynyl methanesulfonate 在 sodium azide 作用下， 以 甲醇 为溶剂， 生成 1,14-diazidotetradec-5-yne
  参考文献：
  名称：

  New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation

  摘要：

  Derivatives of 5-(4-an-nobutyl)-2-thiophene-octylamine, a potent polyamine-sensitive inhibitor of the NMDA receptor, were synthesized and evaluated as inhibitors of [H-3]MK-801 binding to rat brain membranes. Alkylations of the terminal amino groups reduced inhibitory potency; only incorporation of the amino group of the short 4-aminobutyl arm into a piperidine ring was tolerated. Substitution of the thiophene nucleus with methyl or ethyl, and its replacement by a benzene nucleus, was of minor influence. The corresponding diguanidines exhibited high potency independent of chain length, whereas their sensitivity to spermine was sharply dependent on chain length. Insertion of an amide bond into the long octylamine arm increased sensitivity to spermine and to Tris buffer. Our results indicate that spermine sensitivity of [H-3]MK-801 binding inhibition is responsive to subtle changes in inhibitor structure and represents a promising target for pharmaceutical research. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.017
• 作为产物：
  描述：

  1-溴-8-(四氢吡喃氧基)辛烷 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 14-Methylsulfonyloxytetradec-9-ynyl methanesulfonate
  参考文献：
  名称：

  New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation

  摘要：

  Derivatives of 5-(4-an-nobutyl)-2-thiophene-octylamine, a potent polyamine-sensitive inhibitor of the NMDA receptor, were synthesized and evaluated as inhibitors of [H-3]MK-801 binding to rat brain membranes. Alkylations of the terminal amino groups reduced inhibitory potency; only incorporation of the amino group of the short 4-aminobutyl arm into a piperidine ring was tolerated. Substitution of the thiophene nucleus with methyl or ethyl, and its replacement by a benzene nucleus, was of minor influence. The corresponding diguanidines exhibited high potency independent of chain length, whereas their sensitivity to spermine was sharply dependent on chain length. Insertion of an amide bond into the long octylamine arm increased sensitivity to spermine and to Tris buffer. Our results indicate that spermine sensitivity of [H-3]MK-801 binding inhibition is responsive to subtle changes in inhibitor structure and represents a promising target for pharmaceutical research. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.017

文献信息

• New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation
  作者：Thomas Pöhler、Oliver Schadt、Daniela Niepel、Patrick Rebernik、Michael L. Berger、Christian R. Noe

  DOI：10.1016/j.ejmech.2006.09.017

  日期：2007.2

  Derivatives of 5-(4-an-nobutyl)-2-thiophene-octylamine, a potent polyamine-sensitive inhibitor of the NMDA receptor, were synthesized and evaluated as inhibitors of [H-3]MK-801 binding to rat brain membranes. Alkylations of the terminal amino groups reduced inhibitory potency; only incorporation of the amino group of the short 4-aminobutyl arm into a piperidine ring was tolerated. Substitution of the thiophene nucleus with methyl or ethyl, and its replacement by a benzene nucleus, was of minor influence. The corresponding diguanidines exhibited high potency independent of chain length, whereas their sensitivity to spermine was sharply dependent on chain length. Insertion of an amide bond into the long octylamine arm increased sensitivity to spermine and to Tris buffer. Our results indicate that spermine sensitivity of [H-3]MK-801 binding inhibition is responsive to subtle changes in inhibitor structure and represents a promising target for pharmaceutical research. (c) 2006 Elsevier Masson SAS. All rights reserved.