2,4-diphenyl-1,2,4-thiadiazoline-3,5-dione | 7707-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-diphenyl-1,2,4-thiadiazoline-3,5-dione
• 英文别名: 2,4-diphenyl-[1,2,4]thiadiazolidine-3,5-dione；2,4-Diphenyl-<1,2,4>thiadiazolidin-3,5-dion；2,4-Diphenyl-1,2,4-thiadiazolidine-3,5-dione
• CAS: 7707-46-2
• 化学式: C₁₄H₁₀N₂O₂S
• 分子量: 270.312
• InChiKey: UJEBRSNVLSQUBC-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  397.6±25.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-diphenyl-1,2,4-thiadiazoline-3,5-dione 在 L-半胱氨酸 、 carbonic anhydrase 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 生成 硫化氢
  参考文献：
  名称：

  硫醇激活的 1,2,4-Thiadiazolidin-3,5-diones 通过羰基硫化物依赖途径释放硫化氢

  摘要：

  最近的努力扩大了释放重要的生物信号分子硫化氢 (H 2 S) 的小分子供体的开发。先前关于 1,2,4-thiadiazolidin-3,5-diones (TDZNs) 的研究报告称，这些化合物会直接释放 H 2 S，尽管效率低下。然而，TDZNs在离体主动脉环松弛模型中显示出对 H 2 S 介导的松弛有希望的功效。在这里，我们表明 TDZN 可有效释放硫化羰 (COS)，后者可通过碳酸酐酶 (CA)转化为 H 2 S，而不是像之前报道的那样直接释放 H 2 S。

  DOI：

  10.1021/acs.joc.2c01220
• 作为产物：
  描述：

  S-chloro-N-phenylisothiocarbamoyl chloride 在 水 作用下， 生成 2,4-diphenyl-1,2,4-thiadiazoline-3,5-dione
  参考文献：
  名称：

  Ottmann,G.; Hooks,H., Angewandte Chemie, 1966, vol. 78, p. 681

  摘要：

  DOI：

文献信息

• 1,2,4-Thiadiazolidin-3,5-diones as novel hydrogen sulfide donors
  作者：Beatrice Severino、Angela Corvino、Ferdinando Fiorino、Paolo Luciano、Francesco Frecentese、Elisa Magli、Irene Saccone、Paola Di Vaio、Valentina Citi、Vincenzo Calderone、Luigi Servillo、Rosario Casale、Giuseppe Cirino、Valentina Vellecco、Mariarosaria Bucci、Elisa Perissutti、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1016/j.ejmech.2017.10.068

  日期：2018.1

  Hydrogen sulfide (H2S) is an endogenous modulator that plays significant physio-pathological roles in several biological systems. In this research field there is a large interest in developing selective CBS and CSE inhibitors and H2S releasing moieties, that could be either used as therapeutic agents or linked to known drugs. One of the major problem is the limited availability of chemicals that ensure a controlled release of H2S in vitro as well in vivo. Aiming to obtain novel H2S donors, whose release properties could be appropriately modulated, we have synthesized a series of 1,2,4-thiadiazolidine-3,5-diones (THIA 1-10) as innovative donors that could release H2S in controlled manner. All the synthesized compounds were evaluated for their H2S releasing properties by an amperometric approach and for their vasorelaxant ability on aorta rings. In order to rationalize the obtained results, a detailed study on the release mechanism has been performed using the most efficient H2S donor, THIA 3 (C-max 65.4 mu M and EC50 1.7 mu M). 2017 Elsevier Masson SAS. All rights reserved.
• Slomczynska, Urszula; Barany, George, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 241 - 246
  作者：Slomczynska, Urszula、Barany, George

  DOI：——

  日期：——
• SLOMCZYNSKA, U.;BARANY, G., J. HETEROCYCL. CHEM., 1984, 21, N 1, 241-246
  作者：SLOMCZYNSKA, U.、BARANY, G.

  DOI：——

  日期：——
• Ottmann,G.; Hooks,H., Angewandte Chemie, 1966, vol. 78, p. 681
  作者：Ottmann,G.、Hooks,H.

  DOI：——

  日期：——
• Thiol-Activated 1,2,4-Thiadiazolidin-3,5-diones Release Hydrogen Sulfide through a Carbonyl-Sulfide-Dependent Pathway
  作者：Haley M. Smith、Michael D. Pluth

  DOI：10.1021/acs.joc.2c01220

  日期：2022.9.16

  important biological signaling molecule hydrogen sulfide (H2S). Previous work on 1,2,4-thiadiazolidin-3,5-diones (TDZNs) reported that these compounds release H2S directly, albeit inefficiently. However, TDZNs showed promising efficacy in H2S-mediated relaxation in ex vivo aortic ring relaxation models. Here, we show that TDZNs release carbonyl sulfide (COS) efficiently, which can be converted to H2S

  最近的努力扩大了释放重要的生物信号分子硫化氢 (H 2 S) 的小分子供体的开发。先前关于 1,2,4-thiadiazolidin-3,5-diones (TDZNs) 的研究报告称，这些化合物会直接释放 H 2 S，尽管效率低下。然而，TDZNs在离体主动脉环松弛模型中显示出对 H 2 S 介导的松弛有希望的功效。在这里，我们表明 TDZN 可有效释放硫化羰 (COS)，后者可通过碳酸酐酶 (CA)转化为 H 2 S，而不是像之前报道的那样直接释放 H 2 S。