N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane | 206991-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane
• 英文别名: N-Ethyl-N-[3-[(mesitylsulfonyl)amino]propyl]-2,4,6-trimethylbenzenesulfonamide；N-[3-[ethyl-(2,4,6-trimethylphenyl)sulfonylamino]propyl]-2,4,6-trimethylbenzenesulfonamide
• CAS: 206991-72-2
• 化学式: C₂₃H₃₄N₂O₄S₂
• 分子量: 466.666
• InChiKey: BMZQDECLRKFMRK-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  615.5±65.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.5h， 生成 N¹,N¹²-diethyl-6-phthalimido-N¹,N⁴,N⁹,N¹²-tetrakis(mesitylenesulfonyl)spermine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Aminopolyamines

  摘要：

  Exploitation of the polyamine backbone as a vector for intracellular transport of various pharmacophores has focused largely on fixing the cargo molecule to one of the nitrogens in the linear chain. This communication describes the assembly of a model aminopolyamine analogue, 6-amino-N-1,N-12-diethylspermine, and its biological properties. This amino polyamine presents an additional site of attachment for cargo molecules, reduces cell growth, and achieves cellular concentrations that are higher than those of N-1,N-12-diethylspermine.

  DOI：

  10.1021/jm050024m
• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 N-乙基-1,3-丙二胺 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以88%的产率得到N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane
  参考文献：
  名称：

  羟基化多胺类似物作为抗增殖剂的合成和评价。

  摘要：

  一种访问N（1）-环丙基甲基-N（11）-乙基去甲精胺（CPMENSPM）的新方法和（2R，10S）-N（1）-环丙基甲基-2,10-二羟基-N（11）-的首次合成描述了乙基去甲精胺[（2R，10S）-（HO）（2）CPMENSPM]。与N（1），N（11）-diethylnorspermine（DENSPM）或（2R，10R）-N（1），N（11）-相比，这两种多胺类似物均对L1210鼠白血病细胞的生长更具活性。处理96小时后，生成2,10-二羟基去甲精胺二乙基[（2R，10R）-（HO）（2）DENSPM]；在96小时时，该活性可与（2S，10S）-N（1），N（11）-二乙基-2,10-二羟基去甲精胺[（2S，10S）-（HO）（2）DENSPM]媲美。两种环丙基化合物都可以减少腐胺和亚精胺库，但效果不如DENSPM及其衍生物。仅CPMENSPM，而不是（2R，10S）-（HO）（2

  DOI：

  10.1021/jm000532q
• 作为试剂：
  描述：

  (Z)-2-butene-1,4-diyl-bis(mesitylenesulfonate) 、 N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane 在 N,N'-bis(mesitylenesulfonyl)-N-ethyl-1,3-diaminopropane 作用下， 以92的产率得到(Z)-3,7,12,16-tetrakis(mesitylenesulfonyl)-3,7,12,16-tetraazaoctadec-9-ene
  参考文献：
  名称：

  J. Med. Chem. 1998, 41, 4723-4732

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of unsymmetrical polyamine derivatives as antitumor agents
  作者：Jianhong Wang、Songqiang Xie、Yanjie Li、Yongjun Guo、Yuanfang Ma、Jin Zhao、Otto Phanstiel、Chaojie Wang

  DOI：10.1016/j.bmc.2008.05.035

  日期：2008.7

  counterpart 1. The ornithine decarboxylase and topoisomerase II inhibition experiments indicated that ODC and TOPO II were potential, but not unique targets of these conjugates. Furthermore, the in vivo antitumor activities illustrated that the representative conjugate 2f and the homospermidine analogue 1 evidently inhibited the tumor growth and significantly increased the survival time of mice-bearing

  制备了一系列不对称取代的多胺衍生物，并研究了它们在小鼠白血病L1210，黑色素瘤B16和HeLa细胞中的细胞毒性。体外细胞毒性表明，这些缀合物可以识别多胺转运蛋白，并且与未取代的对应物相比，即使引入末端烷基导致细胞毒性降低，N-乙基修饰的高精胺部分也可能作为高精胺成为另一种有效载体。鸟氨酸脱羧酶和拓扑异构酶II抑制实验表明ODC和TOPO II是潜在的，但不是这些结合物的唯一靶标。此外，
• [EN] CONFORMATIONALLY RESTRICTED POLYAMINES AND THEIR USE AS ANTINEOPLASTIC AGENTS<br/>[FR] POLYAMINES DE CONFORMATION RESTREINTE ET LEUR UTILISATION EN TANT QU'AGENTS ANTINEOPLASIQUES
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：WO1998017624A1

  公开（公告）日：1998-04-30

  (EN) Compounds of the Formula (I): E-NH-D-NH-B-A-B-NH-D-NH-E, wherein A is C2-C6 alkene, C3-C6 cycloalkyl, cycloalkenyl, or cycloaryl; B is independently a single bond, C1-C6 alkyl alkenyl; D is independently C1-C6 alkyl or alkenyl, or C3-C6 cycloalkyl, cycloalkenyl, or cycloaryl; and E is independently H, C1-C6 alkyl or alkenyl; and pharmaceutically suitable salts thereof; a synthetic method therefor, pharmaceutical dosage forms containing one of more of these compounds, and use of these compounds in the treatment of neoplastic cell growth, are disclosed.(FR) Composés représentés par la formule (I): E-NH-D-NH-B-A-B-NH-D-NH-E dans laquelle A représente alkène C2-C6, cycloalkyle C3-C6, cycloalkényle ou cycloaryle; B représente indépendamment une liaison simple, alkylalkényle C1-C6; D représente indépendamment alkyle C1-C6 ou alkényle ou cycloalkyle C3-C6, cycloalkényle ou cycloaryle; E représente indépendamment H, alkyle C1-C6 ou alkényle; leurs sels acceptables sur le plan pharmaceutique; leur procédé de synthèse, formes galéniques pharmaceutiques contenant un ou plusieurs de ces composés et utilisation de ces composés pour la traitement de la prolifération cellulaire néoplasique.

  化合物的公式(I)为：E-NH-D-NH-B-A-B-NH-D-NH-E，其中A为C2-C6烯烃，C3-C6环烷基，环烯基或环芳基；B独立地为单键，C1-C6烷基烯基；D独立地为C1-C6烷基或烯基，或C3-C6环烷基，环烯基或环芳基；E独立地为H，C1-C6烷基或烯基；以及其在药学上适用的盐；公开了一种合成方法，含有其中一个或多个化合物的药物剂量形式，以及使用这些化合物治疗肿瘤细胞生长的方法。
• Conformationally Restricted Analogues of ¹<i>N</i>,¹²<i>N</i>-Bisethylspermine:  Synthesis and Growth Inhibitory Effects on Human Tumor Cell Lines
  作者：Venodhar K. Reddy、Aldonia Valasinas、Aparajita Sarkar、Hirak S. Basu、Laurence J. Marton、Benjamin Frydman

  DOI：10.1021/jm980172v

  日期：1998.11.1

  Eight analogues of N-1,N-12-bisethylspermine (BES) with restricted conformations were synthesized in the search for new spermine mimetics with cytotoxic activities. By replacing the central butane segment of BES with a 1,2-disubstituted cyclopropane ring, a pair of cis/trans-isomers was obtained that introduced a spatial constraint in the otherwise freely mobile butane chain. An analogous pair of isomers was obtained when the butane segment was replaced with a 1,2-disubstituted cyclobutane ring or with a 2-butene residue. The six new BES analogues thus obtained.(three pairs of cis/trans-isomers) were growth inhibitory at low-micromolar concentrations against four human tumor cell lines (A549, HT-29, U251MG, and DU145) but were less growth inhibitory against two other human tumor cell lines (PC-3 and MCF7). N-1,N-12-Bisethylspermyne, where the central butane segment of BES was replaced by the rigid 2-butyne segment, was devoid of growth inhibitory activity against five of the six human cell lines studied (DU145 being the only exception), a clear indication of the importance of conformational mobility at the N-4,N-9-butane segment of BES for its biological activity. When the butane segment was replaced by a benzene-1,2-dimethyl residue, the resulting BES analogue was devoid of growth inhibitory activity despite its cisoid conformation. The cytotoxicity of the analogues does not seem to be directly related to their uptake by the cells or to their effects on cellular polyamine levels. BES analogues with restricted conformations but which contained the equivalent of a two-carbon unit, rather than the natural four-carbon unit, at the central segment, such as 1,2-diaminocyclopropyl or 1,2-diaminocyclobutyl derivatives, were devoid of growth inhibitory effects at the concentrations studied. The development of conformationally restricted polyamine analogues appears to show promise in the further quest for polyamine-related therapeutic agents with specificity of action.
• CONFORMATIONALLY RESTRICTED POLYAMINES AND THEIR USE AS ANTINEOPLASTIC AGENTS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0934249B1

  公开（公告）日：2002-03-27
• WO2006/52229
  申请人：——

  公开号：——

  公开（公告）日：——