Acetamino-decyl-malonsaeure-diaethylester | 6955-17-5

• 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: Acetamino-decyl-malonsaeure-diaethylester
• 英文别名: Diethyl(acetylamino)(decyl)propanedioate；diethyl 2-acetamido-2-decylpropanedioate
• CAS: 6955-17-5
• 化学式: C₁₉H₃₅NO₅
• 分子量: 357.491
• InChiKey: DUQBDSVPGRJHKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetamino-decyl-malonsaeure-diaethylester 在 盐酸 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl α-aminododecanoate hydrochloride
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：
• 作为产物：
  描述：

  癸基溴 、 乙酰氨基丙二酸二乙酯 在 乙醇 、 sodium 作用下， 生成 Acetamino-decyl-malonsaeure-diaethylester
  参考文献：
  名称：

  亲脂性肽核上的聚阳离子树状聚合物的合成，用于寡核苷酸的络合和运输。

  摘要：

  完成了新型聚阳离子亲脂性肽核的合成，并且这些试剂在与寡核苷酸复合后成功地用ODN1转染了人视网膜色素上皮细胞。与转染剂cytofectin GSV相比，hVEGF蛋白（人血管内皮生长因子）产量的降低间接地测量了转染水平。

  DOI：

  10.1016/s0960-894x(02)00511-5

文献信息

• Syntheses of Polycationic Dendrimers on Lipophilic Peptide Core for Complexation and Transport of Oligonucleotides
  作者：Norbert Wimmer、Robert J. Marano、Philip S. Kearns、Elizabeth P. Rakoczy、Istvan Toth

  DOI：10.1016/s0960-894x(02)00511-5

  日期：2002.9

  Synthesis of novel polycationic lipophilic peptide core(s) was accomplished and these agents successfully transfected human retinal pigment epithelium cells with ODN1 upon complexation with the oligonucleotide. The level of transfection was indirectly measured by the decreased production of the protein hVEGF (human vascular endothelial growth factor) in comparison to the transfection agent cytofectin

  完成了新型聚阳离子亲脂性肽核的合成，并且这些试剂在与寡核苷酸复合后成功地用ODN1转染了人视网膜色素上皮细胞。与转染剂cytofectin GSV相比，hVEGF蛋白（人血管内皮生长因子）产量的降低间接地测量了转染水平。
• Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis
  作者：Diego Veras Wilke、Paula Christine Jimenez、Renata Mendonça Araújo、Wildson Max Barbosa da Silva、Otília Deusdênia Loiola Pessoa、Edilberto Rocha Silveira、Claudia Pessoa、Manoel Odorico de Moraes、Mariusz Skwarczynski、Pavla Simerska、Istvan Toth、Letícia Veras Costa-Lotufo

  DOI：10.1016/j.bmc.2010.09.027

  日期：2010.11

  Lipidic alpha-amino acids (LAAs) have been described as non-natural amino acids with long saturated or unsaturated aliphatic chains. In the continuing prospect to discover anticancer agents from marine sources, we have obtained a mixture of two cytotoxic LAAs (1a and 1b) from the zoanthid Protopalythoa variabilis. The anti-proliferative potential of 14 synthetic LAAs and 1a/1b were evaluated on four tumor cell lines (HCT-8, SF-295, MDA-MB-435, and HL-60). Five of the synthetic LAAs showed high percentage of tumor cell inhibition, while 1a/1b completely inhibited tumor cell growth. Additionally, apoptotic effects of 1a/1b were studied on HL-60 cell line. 1a/1b-treated cells showed apoptosis morphology, loss of mitochondrial potential, and DNA fragmentation. (C) 2010 Elsevier Ltd. All rights reserved.
• 2-Aminohydroxamic acid derivatives as inhibitors of Bacillus cereus phosphatidylcholine preferred phospholipase C PC-PLCBc
  作者：Patricia González-Bulnes、Albert González-Roura、Daniel Canals、Antonio Delgado、Josefina Casas、Amadeu Llebaria

  DOI：10.1016/j.bmc.2010.10.031

  日期：2010.12

  Phosphatidylcholine preferring phospholipase C (PC-PLC) is an important enzyme that plays a key role in a variety of cellular events and lipid homoeostases. Bacillus cereus phospholipase C (PC-PLCBc) has antigenic similarity with the elusive mammalian PC-PLC, which has not thus far been isolated and purified. Therefore the discovery of inhibitors of PC-PLCBc is of current interest. Here, we describe the synthesis and biological evaluation of a new type of compounds inhibiting PC-PLCBc. These compounds have been designed by evolution of previously described 2-aminohydroxamic acid PC-PLCBc inhibitors that block the enzyme by coordination of the zinc active site atoms present in PC-PLCBc [Gonzalez-Roura, A.; Navarro, I.; Delgado, A.; Llebaria, A.; Casas, J. Angew. Chem. Int. Ed. 2004, 43, 862]. The new compounds maintain the zinc coordinating groups and possess an extra trimethylammonium function, linked to the hydroxyamide nitrogen by an alkyl chain, which is expected to mimic the trimethylammonium group of the phosphatidylcholine PC-PLCBc substrates. Some of the compounds described inhibit the enzyme with IC50's in the low micromolar range. Unexpectedly, the most potent inhibitors found are those that possess a trimethylammonium group but have chemically blocked the zinc coordinating functionalities. The results obtained suggest that PC-PLCBc inhibition is not due to the interaction of compounds with the phospholipase catalytic zinc atoms, but rather results from the inhibitor cationic group recognition by the PC-PLCBc amino acids involved in choline lipid binding. (C) 2010 Elsevier Ltd. All rights reserved.
• Potent Immunosuppressants, 2-Alkyl-2-aminopropane-1,3-diols
  作者：Tetsuro Fujita、Ryoji Hirose、Masahiko Yoneta、Shigeo Sasaki、Kenichiro Inoue、Masatoshi Kiuchi、Susumu Hirase、Kenji Chiba、Hiroshi Sakamoto、Masafumi Arita

  DOI：10.1021/jm960391l

  日期：1996.1.1

  Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft, survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.
• Substituted Acetamidomalonic Esters and dl-2-Acetamido Acids as Antitumor Agents
  作者：John Andrako、J. Doyle Smith、Walter H. Hartung

  DOI：10.1002/jps.2600500413

  日期：1961.4