methanesulfonic acid, 3-azido-3-methylbutyl ester | 252353-46-1

• 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: methanesulfonic acid, 3-azido-3-methylbutyl ester
• 英文别名: 3-Azido-3-methylbutyl methanesulfonate；(3-azido-3-methylbutyl) methanesulfonate
• CAS: 252353-46-1
• 化学式: C₆H₁₃N₃O₃S
• 分子量: 207.254
• InChiKey: VLRXCZZAVKJQJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid, 3-azido-3-methylbutyl ester 在 palladium on activated charcoal sodium azide 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 正丁醇 为溶剂， 45.0 ℃ 、400.0 kPa 条件下， 反应 83.0h， 生成 N¹-[6-[(aminoiminomethyl)amino]hexyl]-N³-[4-[(3-amino-2-methylbutyl)amino]butyl]propanediamide, tris(trifluoroacetate)
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 sodium azide 、 dimethyl sulfide borane 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methanesulfonic acid, 3-azido-3-methylbutyl ester
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x

文献信息

• Benzimidazole derivatives
  申请人：——

  公开号：US20040044056A1

  公开（公告）日：2004-03-04

  This invention relates to the compounds represented by a general formula [I]: 1 [in which A 1 and A 2 represent optionally fluorine-substituted methine or the like; B represents halogen, cyano, lower alkyl or the like; D represents optionally substituted heterocyclic group or the like; and G represents C 3 -C 20 aliphatic group such as alicyclic group]. These compounds inhibit nociceptin activities due to their high affinity to nociceptin receptor, and are useful as analgesic, antiobestic, corebral function improver, drugs for treatment of alzheimer's disease and dementia, remedies for schizophrenia and neurodegenerative diseases, antidepressant, remedies for diabetes insipidus, polyuria, hypotension and so on.

  本发明涉及由一般式[I]表示的化合物：1[其中，A1和A2表示选择性氟代甲基或类似物；B表示卤素，氰基，低碳烷基或类似物；D表示选择性取代的杂环基团或类似物；G表示C3-C20脂肪族基团，例如脂环族基团]。这些化合物由于对痛觉受体具有高亲和力而抑制了痛觉肽活性，并且可用作镇痛剂，抗肥胖剂，脑功能改善剂，治疗阿尔茨海默病和痴呆症的药物，治疗精神分裂症和神经退行性疾病的药物，抗抑郁剂，治疗尿崩症，多尿症，低血压等的药物。
• Antimicrobial N-chlorinated compositions
  申请人：Novabay Pharmaceuticals, Inc.

  公开号：US08278482B2

  公开（公告）日：2012-10-02

  The present application relates to N-chlorinated cationic compounds of Formula I or a salt thereof, and associated compositions and methods of use as antimicrobial agents.

  本申请涉及到公式I的N-氯化阳离子化合物或其盐，以及相关的组合物和用作抗微生物剂的方法。
• ANTIMICROBIAL N-CHLORINATED COMPOSITIONS
  申请人：Jain Rakesh K.

  公开号：US20100158818A1

  公开（公告）日：2010-06-24

  The present application relates to N-chlorinated cationic compounds of Formula I or a salt thereof, and associated compositions and methods of use as antimicrobial agents.

  本申请涉及式I的N-氯化阳离子化合物或其盐，以及相关组合物和用作抗微生物剂的方法。
• BENZIMIDAZOLE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP1342717A1

  公开（公告）日：2003-09-10

  This invention relates to the compounds represented by a general formula [I]:    [in which A1 and A2 represent optionally fluorine-substituted methine or the like; B represents halogen, cyano, lower alkyl or the like; D represents optionally substituted heterocyclic group or the like; and G represents C3-C20 aliphatic group such as alicyclic group]. These compounds inhibit nociceptin activities due to their high affinity to nociceptin receptor, and are useful as analgesic, antiobestic, corebral function improver, drugs for treatment of alzheimer's disease and dementia, remedies for schizophrenia and neurodegenerative diseases, antidepressant, remedies for diabetes insipidus, polyuria, hypotension and so on.

  本发明涉及通式[I]所代表的化合物： [其中 A1 和 A2 代表任选氟取代的甲基或类似物；B 代表卤素、氰基、低级烷基或类似物；D 代表任选取代的杂环基团或类似物；G 代表 C3-C20 脂肪族基团，例如脂环族基团]。这些化合物由于与痛觉素受体的高亲和力而抑制痛觉素的活性，可用作镇痛剂、抗镇静剂、改善大脑核心功能的药物、治疗老年痴呆症和痴呆症的药物、治疗精神分裂症和神经退行性疾病的药物、抗抑郁剂、治疗糖尿病、多尿、低血压等。
• US6969712B2
  申请人：——

  公开号：US6969712B2

  公开（公告）日：2005-11-29