N-(2-ethylthioethyl)iminodiacetic acid | 82793-88-2

• 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: N-(2-ethylthioethyl)iminodiacetic acid
• 英文别名: ethylmercaptoethyliminodiacetic acid；2-[Carboxymethyl(2-ethylsulfanylethyl)amino]acetic acid
• CAS: 82793-88-2
• 化学式: C₈H₁₅NO₄S
• 分子量: 221.277
• InChiKey: XYVVSAKNDRNLEL-UHFFFAOYSA-N

物化性质

• 沸点：
  420.1±40.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-ethylthioethyl)iminodiacetic acid 在 4-二甲氨基吡啶 、 氢氟酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.33h， 生成 [{[6-((7R,8R,9S,13S,14S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl)-hexylcarbamoyl]-methyl}-(2-ethylsulfanyl-ethyl)-amino]-acetic acid
  参考文献：
  名称：

  7α- and 17α-Substituted estrogens containing tridentate tricarbonyl rhenium/Technetium complexes: synthesis of estrogen receptor imaging agents and evaluation using microPET with technetium-94m

  摘要：

  To develop technetium and rhenium-labeled imaging agents for estrogen receptor (ER) positive breast tumors, we have prepared tridentate metal tricarbonyl chelates substituted at the 7alpha- and 17alpha-positions of estradiol. Some of the Re(CO)(3) conjugates have high binding for the ER in vitro. The in vivo biodistribution of the highest affinity of these novel metal tricarbonyl conjugates, prepared as the Tc-94m labeled analogue, was evaluated by tissue dissection and microPET imaging. Although target tissue-selective uptake was not apparent, it is notable that microPET imaging identified the stomach as a major site of activity deposition, a site that might have been missed by standard tissue distribution studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.004
• 作为产物：
  描述：

  2-氯乙基乙基硫醚 、 亚氨基二乙酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以46%的产率得到N-(2-ethylthioethyl)iminodiacetic acid
  参考文献：
  名称：

  7α- and 17α-Substituted estrogens containing tridentate tricarbonyl rhenium/Technetium complexes: synthesis of estrogen receptor imaging agents and evaluation using microPET with technetium-94m

  摘要：

  To develop technetium and rhenium-labeled imaging agents for estrogen receptor (ER) positive breast tumors, we have prepared tridentate metal tricarbonyl chelates substituted at the 7alpha- and 17alpha-positions of estradiol. Some of the Re(CO)(3) conjugates have high binding for the ER in vitro. The in vivo biodistribution of the highest affinity of these novel metal tricarbonyl conjugates, prepared as the Tc-94m labeled analogue, was evaluated by tissue dissection and microPET imaging. Although target tissue-selective uptake was not apparent, it is notable that microPET imaging identified the stomach as a major site of activity deposition, a site that might have been missed by standard tissue distribution studies. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.004

文献信息

• Organometallic [Re(CO)₃]⁺and [Re(CO)₂(NO)]²⁺Labeled Substrates for Human Thymidine Kinase 1
  作者：Harriet Struthers、Adelheid Hagenbach、Ulrich Abram、Roger Schibli

  DOI：10.1021/ic9000126

  日期：2009.6.15

  Thymidine was functionalized at position N3 with a tridentate iminodiacetic acid chelating system and a potentially tetradentate mercaptoethyliminodiacetic acid chelating system. Spacers of different lengths (ethyl and butyl) were introduced between the chelators and thymidine, The derivatives were labeled with the [Re(CO)(2)(NO)](2+) and [Re(CO)(3)](+) cores to give isostructural complexes with different overall charges. All complexes were analyzed by NMR, MS, and IR, and in addition, the X-ray structure of a [Re(CO)(2)(NO)](2+) labeled thymidine derivative functionalized at the N3 position was solved. The ligands incorporating the potentially tetradentate mercaptoethyliminodiacetic acid chelating system coordinated tridentately through iminodiacetic acid to both the [Re(CO)(2)(NO)](2+) core and the [Re(CO)(3)](+) core. This was surprising given that the reaction of [NEt4][Re(CO)(2)(NO)Br-3] with the model ligand ethylmercaptoethyliminodiacetic acid led to dissociation of a carbonyl ligand and formation of a monocarbonyl-mononitrosyl complex, as confirmed by X-ray structure analysis. All of the organometallic thymidine derivatives were substrates for human thymidine kinase 1, a key enzyme in (cancer) cell proliferation. Neutral [Re(CO)(2)(NO)](2+) labeled thymidine derivatives revealed substrate activity ranging from 24 to 40%, and the structurally analogous anionic [Re(CO)(3)](+) labeled thymidine derivatives from 20 to 38% compared with the natural substrate thymidine.
• 7α- and 17α-Substituted estrogens containing tridentate tricarbonyl rhenium/Technetium complexes: synthesis of estrogen receptor imaging agents and evaluation using microPET with technetium-94m
  作者：Leonard G. Luyt、Heather M. Bigott、Michael J. Welch、John A. Katzenellenbogen

  DOI：10.1016/j.bmc.2003.09.004

  日期：2003.11

  To develop technetium and rhenium-labeled imaging agents for estrogen receptor (ER) positive breast tumors, we have prepared tridentate metal tricarbonyl chelates substituted at the 7alpha- and 17alpha-positions of estradiol. Some of the Re(CO)(3) conjugates have high binding for the ER in vitro. The in vivo biodistribution of the highest affinity of these novel metal tricarbonyl conjugates, prepared as the Tc-94m labeled analogue, was evaluated by tissue dissection and microPET imaging. Although target tissue-selective uptake was not apparent, it is notable that microPET imaging identified the stomach as a major site of activity deposition, a site that might have been missed by standard tissue distribution studies. (C) 2003 Elsevier Ltd. All rights reserved.