(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one-3-(2',3'-dibromopropionyl) | 473907-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one-3-(2',3'-dibromopropionyl)
• 英文别名: (4S,5R)-1-(2,3-dibromopropanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 473907-77-6
• 化学式: C₁₄H₁₆Br₂N₂O₂
• 分子量: 404.101
• InChiKey: DVHQIEFEDPMAGC-VAGKLZBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one-3-(2',3'-dibromopropionyl) 在 氨 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (4R,5S,2'R,2''S)-1,5-dimethyl-3-{[1'-(2''-acetamido-4''-methylpentanoyl)-2'-aziridinyl]carbonyl}-4-phenylimidazolidin-2-one
  参考文献：
  名称：

  Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

  摘要：

  The ring expansion of 3-unsubstituted (R)-aziridine-2-imide-containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00989-8
• 作为产物：
  描述：

  (4R,5S)-1,5-dimethyl-4-phenyl-3-(2-propenoyl)-2-imidazolidinone 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one-3-(2',3'-dibromopropionyl)
  参考文献：
  名称：

  Dipeptides containing D-serine or D-isoserine from the same (R)-aziridine-2-imide by a simple reversal of the synthetic procedure

  摘要：

  The ring expansion of 3-unsubstituted (R)-aziridine-2-imide-containing dipeptide under acidic conditions gives rise to oxazoline-5-imide regio and stereoselectively, which can be hydrolysed to the dipeptide containing D-isoserine. On the other hand, the ring opening of 3-unsubstituted (R)-aziridine-2-ester dipeptide, easily obtained from the same (R)-aziridine, gives the regioisomeric dipeptide containing D-serine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00989-8

文献信息

• Synthetic cofactor analogs of S-adenosylmethionine as ligatable probes of biological methylation and methods for their use
  申请人：Rajski R. Scott

  公开号：US20070161007A1

  公开（公告）日：2007-07-12

  The present invention discloses compounds and methods used to specifically target substrates of methylation by S-adenosyl-L-methionine (SAM)-dependent methyltransferases. The substrates can be peptides, single stranded nucleic acids or double stranded nucleic acids, including RNA, DNA and PNA or phospholipids. The compounds disclosed are SAM analogs that are ligated to a methylation site by the methyltransferase. Also disclosed, are reacting groups that are ligatable to the cofactor analogs and can also be used as detectable labels. The reacting group can be used to cleave the substrate providing a methylation footprint. The invention can be used clinically to determine methylation state of a gene or gene promoter such as those involved in imprinting and transcription. In some preferred embodiments, the invention includes a kit, which can include one or more suitable SAM analogs and may include one or more detectable labels. In other preferred embodiments, the invention includes a pharmaceutical composition.

  本发明揭示了化合物和方法，用于特异性靶向S-腺苷基-L-甲硫氨酸（SAM）依赖的甲基转移酶的甲基化底物。这些底物可以是肽、单链核酸或双链核酸，包括RNA、DNA和PNA或磷脂。所揭示的化合物是SAM类似物，它们通过甲基转移酶与甲基化位点连接。此外，还揭示了可与辅因子类似物连接的反应基团，也可用作可检测标记。反应基团可用于裂解底物，提供甲基化足迹。本发明可用于临床上确定基因或基因启动子的甲基化状态，例如涉及印迹和转录的基因。在一些优选实施例中，本发明包括一个试剂盒，其中可以包括一个或多个适当的SAM类似物，也可以包括一个或多个可检测标记。在其他优选实施例中，本发明包括一种制药组合物。
• Expeditious synthesis of aziridine-based cofactor mimics
  作者：Lindsay R Comstock、Scott R Rajski

  DOI：10.1016/s0040-4020(02)00590-2

  日期：2002.7

  S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US7465544B2
  申请人：——

  公开号：US7465544B2

  公开（公告）日：2008-12-16