3-(2-methoxy-ethyl)-2-thioxo-thiazolidin-4-one | 88850-32-2

• 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: 3-(2-methoxy-ethyl)-2-thioxo-thiazolidin-4-one
• 英文别名: 3-(2-Methoxy-aethyl)-2-thioxo-thiazolidin-4-on；3-(2-Methoxyethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 88850-32-2
• 化学式: C₆H₉NO₂S₂
• mdl: MFCD17010306
• 分子量: 191.275
• InChiKey: GWQVMKJMRPYEMR-UHFFFAOYSA-N

物化性质

• 沸点：
  155-160 °C(Press: 20 Torr)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxy-ethyl)-2-thioxo-thiazolidin-4-one 在 乙酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 、 Petroleum ether 为溶剂， 反应 13.0h， 生成 3-(2-Methoxy-ethyl)-5-[2-[1-methyl-1H-pyridin-(2E)-ylidene]-eth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Properties of Bismerocyanines Linked by a 1,8-Naphthylene Skeleton. Novel Solvatochromism Based on Change of Intramolecular Excitonic Coupling Mode

  摘要：

  A newly prepared bismerocyanine linked by a 1,8-naphthylene skeleton has two rotational isomers, syn and anti conformers, with respect to orientation of the two merocyanine chromophores. The NMR studies revealed that a polar solvent such as acetonitrile enhanced a preference for the syn conformer to bring about much larger bathochromic shift of the UV/vis absorption band than that of a 1-naphthyl-substituted merocyanine. The INDO/S-CI calculation indicated that the UV/vis absorption bands of the syn and anti conformers are hypsochromically and bathochromically shifted, respectively, compared to that of the 1-naphthylmerocyanine. Ln accordance with the prediction based on an exciton coupling theory, the anti conformer fluoresces while the syn conformer does not. A polarographic analysis indicated a positive shift of reduction potential and a negative shift of oxidation potential compared to the corresponding value of the 1-naphthylmerocyanine. The shift in the reduction potential of the bismerocyanine relative to the 1-naphthylmerocyanine in acetonitrile was larger than those in chloroform. This was attributed to the difference in the syn/anti ratio.

  DOI：

  10.1021/ja973608p
• 作为产物：
  描述：

  双(羧甲基)三硫代碳酸盐 、 2-甲氧基乙胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 3-(2-methoxy-ethyl)-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  发现有效和口服可生物利用的17β-羟基类固醇脱氢酶3型抑制剂

  摘要：

  先前我们已经报道了衍生自亚苄基恶唑烷二酮和噻唑烷二酮支架的新型3类有效的17β-羟类固醇脱氢酶抑制剂（17β-HSD3）的发现。在这项研究中，这些类似物是在基于人类细胞的分析中进行设计，合成和评估的。建立了围绕该药效团的详细的结构-活性关系（SAR），因此，该系列化合物中的许多化合物在体外均表现出一位数的纳摩尔17β-HDS3抑制活性。为改善口服生物利用度而进行的后续优化工作已通过基于磷酸酯的前药策略针对这些17β-HSD3抑制剂进行了体内概念验证。当以100 mg / kg的高剂量口服磷酸酯16时，图16显示，在促黄体生成激素释放激素（LH-RH）诱导的T产生测定中，相对于阳性对照，有效的睾丸激素（T）降低作用大约两倍。给药后4小时，降低T的作用持续在对照的约10％水平。基于该系列的非甾体分子具有为治疗前列腺癌提供独特而有效的临床机会的潜力。

  DOI：

  10.1016/j.bmc.2012.03.052

文献信息

• Synthesis and antimicrobial evaluation of some 5-(5-nitrofurylidene)rhodanines, 5-(5-nitrofurylidene)thiazolidine-2,4-diones, and their vinylogs
  作者：S. K. Mallick、A. R. Martin、R. G. Lingard

  DOI：10.1021/jm00288a017

  日期：1971.6
• Supersensitization of photographic emulsions with complex merocyanine dyes
  申请人：EASTMAN KODAK CO

  公开号：US02635961A1

  公开（公告）日：1953-04-21
• Versatile Neuromorphic Modulation and Biosensing based on N‐type Small‐molecule Organic Mixed Ionic‐Electronic Conductors
  作者：Riping Liu、Xiuyuan Zhu、Jiayao Duan、Junxin Chen、Zhuang Xie、Chaoyue Chen、Xi Xie、Yanxi Zhang、Wan Yue

  DOI：10.1002/anie.202315537

  日期：2024.1.25

  The ion/chemical‐based modulation feature of organic mixed ionic‐electronic conductors (OMIECs) are critical to advancing next generation bio‐integrated neuromorphic hardware. Despite achievements with polymeric OMIECs in organic electrochemical neuronal synapse (OENS). However, small molecule OMIECs based OENS has not yet been realized. Here, for the first time, we demonstrate an effective materials design concept of combining n‐type fused all‐acceptor small molecule OMIECs with subtle side chain optimization that enables robustly and flexibly modulating versatile synaptic behavior and sensing neurotransmitter in solid or aqueous electrolyte, operating in accumulation modes. By judicious tuning the ending side chains, the linear oligoether and butyl chain derivative gNR‐Bu exhibits higher recognition accuracy for a model artificial neural network (ANN) simulation, higher steady conductance states and more outstanding ambient stability, which is superior to the state‐of‐art n‐type OMIECs based OENS. These superior artificial synapse characteristics of gNR‐Bu can be attributed to its higher crystallinity with stronger ion bonding capacities. More impressively, we unprecedentedly realized n‐type small‐molecule OMIECs based OENS as a neuromorphic biosensor enabling to respond synaptic communication signals of dopamine even at sub‐μM level in aqueous electrolyte. This work may open a new path of small‐molecule ion‐electron conductors for next‐generation ANN and bioelectronics.
• Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors
  作者：Koichiro Harada、Hideki Kubo、Jun Abe、Mari Haneta、Arnel Conception、Shinichi Inoue、Satoshi Okada、Kazuhiko Nishioka

  DOI：10.1016/j.bmc.2012.03.052

  日期：2012.5

  and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg

  先前我们已经报道了衍生自亚苄基恶唑烷二酮和噻唑烷二酮支架的新型3类有效的17β-羟类固醇脱氢酶抑制剂（17β-HSD3）的发现。在这项研究中，这些类似物是在基于人类细胞的分析中进行设计，合成和评估的。建立了围绕该药效团的详细的结构-活性关系（SAR），因此，该系列化合物中的许多化合物在体外均表现出一位数的纳摩尔17β-HDS3抑制活性。为改善口服生物利用度而进行的后续优化工作已通过基于磷酸酯的前药策略针对这些17β-HSD3抑制剂进行了体内概念验证。当以100 mg / kg的高剂量口服磷酸酯16时，图16显示，在促黄体生成激素释放激素（LH-RH）诱导的T产生测定中，相对于阳性对照，有效的睾丸激素（T）降低作用大约两倍。给药后4小时，降低T的作用持续在对照的约10％水平。基于该系列的非甾体分子具有为治疗前列腺癌提供独特而有效的临床机会的潜力。
• Synthesis and Properties of Bismerocyanines Linked by a 1,8-Naphthylene Skeleton. Novel Solvatochromism Based on Change of Intramolecular Excitonic Coupling Mode
  作者：Takashi Katoh、Yoshio Inagaki、Renji Okazaki

  DOI：10.1021/ja973608p

  日期：1998.4.1

  A newly prepared bismerocyanine linked by a 1,8-naphthylene skeleton has two rotational isomers, syn and anti conformers, with respect to orientation of the two merocyanine chromophores. The NMR studies revealed that a polar solvent such as acetonitrile enhanced a preference for the syn conformer to bring about much larger bathochromic shift of the UV/vis absorption band than that of a 1-naphthyl-substituted merocyanine. The INDO/S-CI calculation indicated that the UV/vis absorption bands of the syn and anti conformers are hypsochromically and bathochromically shifted, respectively, compared to that of the 1-naphthylmerocyanine. Ln accordance with the prediction based on an exciton coupling theory, the anti conformer fluoresces while the syn conformer does not. A polarographic analysis indicated a positive shift of reduction potential and a negative shift of oxidation potential compared to the corresponding value of the 1-naphthylmerocyanine. The shift in the reduction potential of the bismerocyanine relative to the 1-naphthylmerocyanine in acetonitrile was larger than those in chloroform. This was attributed to the difference in the syn/anti ratio.