tert-butyl N-[2-[3-[4-(3-aminopropylamino)butylamino]propylamino]-2-oxoethyl]carbamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl N-[2-[3-[4-(3-aminopropylamino)butylamino]propylamino]-2-oxoethyl]carbamate
• 化学式: C₁₇H₃₇N₅O₃
• 分子量: 359.512
• InChiKey: HRIWMWPTGTZDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[3-[4-(3-aminopropylamino)butylamino]propylamino]-2-oxoethyl]carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到N¹-spermine glycinyl amide tetrahydrochloride
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040
• 作为产物：
  描述：

  精胺 、 Boc-甘氨酸-4-硝基苯酯 以 甲醇 为溶剂， 反应 2.0h， 以43%的产率得到tert-butyl N-[2-[3-[4-(3-aminopropylamino)butylamino]propylamino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  Amino Acid/Spermine Conjugates:  Polyamine Amides as Potent Spermidine Uptake Inhibitors

  摘要：

  In this paper we describe the synthesis and characterization of a series of simple spermine/amino acid conjugates, some of which potently inhibit the uptake of spermidine into MDAMB-231 breast cancer cells. The presence of an amide in the functionalized polyamine appeared to add to the affinity for the polyamine transporter. The extensive biological characterization of an especially potent analogue from this series, the Lys-Spm conjugate (31), showed this molecule will be an extremely useful tool for use in polyamine research. It was shown that the use of 31 in combination with DFMO led to a cytostatic growth inhibition of a variety of cancer cells, even when used in the presence of an extracellular source of transportable spermidine. It was furthermore shown that this combination effectively reduced the cellular levels of putrescine and spermidine while not affecting the levels of spermine. These facts together with the nontoxic nature of 31 make it a novel lead for further anticancer development.

  DOI：

  10.1021/jm0101040

文献信息

• MITOGUAZONE FOR PREVENTING THE RELAPSE OR THE PROGRESSION OF MULTIPLE SCLEROSIS
  申请人：Pathologica LLC

  公开号：EP3831372A1

  公开（公告）日：2021-06-09

  Disclosed herein are new oral pharmaceutical compositions of SAMDC inhibitors, polyamine analogs, and polyamine biosynthesis inhibitors, and their application for the treatment of conditions including demyelinating diseases, autoimmune disorders affecting the nervous system, and other neurodegenerative conditions.

  本文公开了SAMDC抑制剂、多胺类似物和多胺生物合成抑制剂的新型口服药物组合物，以及它们在治疗脱髓鞘疾病、影响神经系统的自身免疫性疾病和其他神经退行性疾病等疾病中的应用。
• Methods and compositions for treatment of demyelinating diseases
  申请人：Pathologica LLC

  公开号：US10350178B2

  公开（公告）日：2019-07-16

  Disclosed herein is a method of prevention of progression of a multiple sclerosis in a patient, comprising the administration of methylglyoxal bis(guanylhydrazone) (MGBG) to the patient in need thereof. Also disclosed herein is a method of prevention or reduction in severity of the initiation phase of autoimmune response in a patient having multiple sclerosis, comprising the administration of MGBG to the patient in need thereof.

  本文公开了一种预防多发性硬化症患者病情恶化的方法，包括向有需要的患者施用甲基乙二醛双（鸟苷酸腙）（MGBG）。本文还公开了一种预防多发性硬化症患者自身免疫反应起始阶段或减轻其严重程度的方法，包括对有需要的患者施用 MGBG。
• PHARMACEUTICAL FOR ORAL DELIVERY COMPRISING MGBG AND METHODS OF TREATING DISEASE
  申请人：McKearn John

  公开号：US20110112199A1

  公开（公告）日：2011-05-12

  Disclosed herein are new oral pharmaceutical compositions of MGBG and related polyamine analogs, polyamine biosynthesis inhibitors, polyamine inhibitors of AMD-I and regulators of osteopontin, and their application for the treatment of disease.
• METHODS AND COMPOSITIONS FOR TREATMENT OF DEMYELINATING DISEASES
  申请人：PATHOLOGICA LLC

  公开号：US20150359761A1

  公开（公告）日：2015-12-17

  Disclosed herein are new oral pharmaceutical compositions of SAMDC inhibitors, polyamine analogs, and polyamine biosynthesis inhibitors, and their application for the treatment of conditions including demyelinating diseases, autoimmune disorders affecting the nervous system, and other neurodegenerative conditions.
• US8258186B2
  申请人：——

  公开号：US8258186B2

  公开（公告）日：2012-09-04