N¹,N¹²-dimethylspermine | 113812-18-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹,N¹²-dimethylspermine
• 英文别名: 1,4-Butanediamine, N,N'-bis[3-(methylamino)propyl]-；N,N'-bis[3-(methylamino)propyl]butane-1,4-diamine
• CAS: 113812-18-3
• 化学式: C₁₂H₃₀N₄
• 分子量: 230.397
• InChiKey: RHMQCHCWNFTZMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  48.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N¹,N¹²-dimethyl-N¹,N⁴,N⁹,N¹²-tetratosylspermine 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N¹,N¹²-dimethylspermine
  参考文献：
  名称：

  Synthetic polyamine analogs as antineoplastics

  摘要：

  In this paper, we report on the synthesis and biological activity of a number of N-alkylated spermine compounds. The dialkylspermines N1,N12-dimethylspermine (DMSPM-2), N1,N12-diethylspermine (DESPM-3), and N1,N12-dipropylspermine (DPSPM-4) are all shown to inhibit the growth of L1210 cells in culture with IC50 values of less than 1 microM at 96 h. Furthermore, DESPM-3 is shown to be similarly active against Daudi and HL-60 cells in culture. A structure-activity relationship is shown to exist between the position at which spermine is alkylated and its antiproliferative properties. The activity of 10 microM DESPM-3 against L1210 cells was shown to be cytostatic, with greater than 90% cell viability by trypan blue exclusion, even after a 144-h exposure. When L1210 cells were treated with 10 microM DESPM-3 over a 144-h period, their size and mitochondrial DNA content were gradually but substantially diminished. However, flow cytometric measurements of the nuclear DNA content of these treated cells at 96 h indicated only slightly reduced S and G2 populations and significant changes only after 144 h. A cloning assay performed on the cells after 96 h of exposure to this drug (10 microM) indicated that the cells were not growing. Finally, when male DBA/2 mice, inoculated with L1210 leukemia cells, were treated with DESPM-3, their life span was increased in excess of 200% relative to untreated controls. Moreover, many long-term survivors were apparently tumor free at the end of the experiment (60 days).

  DOI：

  10.1021/jm00401a019

文献信息

• Alkylation of amines
  申请人：Grigg, Ronald Ernest

  公开号：EP0034480A2

  公开（公告）日：1981-08-26

  A process for preparing a N-alkylamine or N, N-dialkylamine, which comprises reacting a primary or secondary amine with a primary or secondary alcohol in the presence of a catalyst selected from iridium, rhodium, ruthenium, osmium, platinum, palladium and rhenium, present either as the metal or a salt or complex thereof. The catalyst is preferably a complex such as RhH(PPh3)4. The process can be used to cause cyclisation, including internal cyclisation so that, by way of example, N-methyl-pyrrolidine may be prepared from (1) pyrrolidine and methanol; (2) 1,4-butanediol and methylamine; and (3) 4-methylamino-1-butanol.

  一种制备 N-烷基胺或 N，N-二烷基胺的工艺，包括在选自铱、铑、钌、锇、铂、钯和铼的催化剂（以金属或其盐或络合物形式存在）存在下，使伯胺或仲胺与伯醇或仲醇反应。催化剂最好是络合物，如 RhH(PPh3)4。该工艺可用于环化，包括内部环化，例如，可从 (1) 吡咯烷和甲醇；(2) 1,4-丁二醇和甲胺；以及 (3) 4-甲基氨基-1-丁醇制备 N-甲基吡咯烷。
• RNA INTERFERENCE IN DERMAL AND FIBROTIC INDICATIONS
  申请人：Phio Pharmaceuticals Corp.

  公开号：EP3560503A1

  公开（公告）日：2019-10-30

  The present invention relates to RNAi constructs with improved tissue and cellular uptake characteristics and methods of use of these compounds in dermal and fibrotic applications.

  本发明涉及具有改进的组织和细胞吸收特性的 RNAi 构建物，以及这些化合物在皮肤和纤维化应用中的使用方法。
• NUCLEIC ACID MOLECULES TARGETING SUPEROXIDE DISMUTASE 1 (SOD1)
  申请人：Phio Pharmaceuticals Corp.

  公开号：EP3862005A1

  公开（公告）日：2021-08-11

  Aspects of the invention relate to methods for treating ALS comprising administering to a subject in need thereof a therapeutically effective amount of a nucleic acid molecule that is directed against a gene encoding superoxide dismutase 1 (SOD1).

  本发明的各个方面涉及治疗 ALS 的方法，包括向有需要的受试者施用治疗有效量的核酸分子，该核酸分子针对编码超氧化物歧化酶 1 (SOD1) 的基因。
• Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids
  申请人：Invivogen

  公开号：EP2674170B1

  公开（公告）日：2014-11-19
• EP3319614B1
  申请人：——

  公开号：EP3319614B1

  公开（公告）日：2020-12-23