2-(Me2NCH2CH2NCH)C4H3S | 120825-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(Me2NCH2CH2NCH)C4H3S
• 英文别名: N,N-dimethyl-2-(thiophen-2-ylmethylideneamino)ethanamine
• CAS: 120825-11-8
• 化学式: C₉H₁₄N₂S
• 分子量: 182.29
• InChiKey: TUNVLEISEPYCQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Me2NCH2CH2NCH)C4H3S 在 溶剂黄146 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

  摘要：

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

  DOI：

  10.1021/acs.jmedchem.6b00752
• 作为产物：
  描述：

  2-噻吩甲醛 、 N,N-二甲基乙二胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-(Me2NCH2CH2NCH)C4H3S
  参考文献：
  名称：

  Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

  摘要：

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

  DOI：

  10.1021/acs.jmedchem.6b00752

文献信息

• Cyclometallated platinum complexes with thienyl imines. X-ray crystal structure of [PtMe{3-(PhCH2NCH)C4H2S}PPh3]
  作者：Craig Anderson、Margarita Crespo、Mercè Font-Bardı́a、Axel Klein、Xavier Solans

  DOI：10.1016/s0022-328x(00)00017-6

  日期：2000.4

  one-electron oxidations always occurred in an irreversible manner and were assigned to oxidation at the platinum center. Oxidative addition of methyl iodide to 4a yielded [PtMe2I3-(Me2NCH2CH2NCH)C4H2S}] (6a), while the reactions of methyl iodide with 4b and 5b each gave mixtures of isomers, arising from oxidative addition with trans stereochemistry followed by isomerization of the resulting platinum(IV) compounds

  的反应[PT 2我4（μ-SMe的2）2 ]与配体3-（ME 2 NCH 2 CH 2 NCH）C 4 H ^ 3 S（图2a）和3-（物理信道2 NCH）C 4 H ^ 3小号（2b）在噻吩环的α位上产生环金属化反应，得到铂（II）络合物[PTMe 3-（Me 2 NCH 2 CH 2 NCH）C 4 H 2 S}]（4a）和[PTMe 3-（PhCH 2 NCH）C 4 H2 S} SMe 2 ]（4b），分别包含[C，N，N']或[C，N]配体。这些化合物与三苯膦反应生成了[PTMe 3-（Me 2 NCH 2 CH 2 NCH）C 4 H 2 S} PPh 3 ]（5a）和[PTMe 3-（PhCH 2 NCH）C 4 H 2 S } PPh 3 ]（5b）。化合物5b在结构上得到了表征。尝试实现配体2-（Me 2 NCH 2 CH 2 NCH）C 4 H的环金属化3 S（2c）和2-（PhCH