5-carboxyethyl-3-(2´-furfurylmethyl)-1,3,5-thiadiazinane-2-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪类
• 英文名称: 5-carboxyethyl-3-(2´-furfurylmethyl)-1,3,5-thiadiazinane-2-thione
• 英文别名: 5-carboxyethyl-3-(2'-furfuryl)-tetrahydro-(2H)-1,3,5-thiazidine-2-thione；3-[5-(Furan-2-ylmethyl)-6-sulfanylidene-1,3,5-thiadiazinan-3-yl]propanoic acid
• 化学式: C₁₁H₁₄N₂O₃S₂
• 分子量: 286.376
• InChiKey: OQXDFWLQBQCZML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-carboxyethyl-3-(2´-furfurylmethyl)-1,3,5-thiadiazinane-2-thione 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 3,5-difurfuryl-2H-1,3,5-thiadiazin-2-thione 、 1,3-(二糠基)硫脲
  参考文献：
  名称：

  Perez; Rodriguez; Perez, Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 9, p. 854 - 857

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 生成 5-carboxyethyl-3-(2´-furfurylmethyl)-1,3,5-thiadiazinane-2-thione
  参考文献：
  名称：

  3,5-二取代的 1,3,5-thiadiazinane-2-thione 衍生物在聚乙二醇 (PEG) 载体上的液相有机合成

  摘要：

  使用可溶性聚合物载体聚乙二醇 (PEG) 5000 通过 PEG 结合的游离氨基的一锅缩合，描述了 3,5-二取代的 1,3,5-噻二嗪烷-2-硫酮衍生物 (THTT) 的高效液相合成酸或 PEG 结合的三肽、二硫代氨基甲酸酯和甲醛在温和条件下。该程序通过简单的后处理程序以良好的收率和高纯度提供目标化合物。这种合成方法还允许有效地制备具有通过 N-3 氮原子连接的两个 THTT 环的新化合物。所有合成化合物的结构均通过标准光谱技术明确确定。

  DOI：

  10.3998/ark.5550190.0013.828

文献信息

• Ochoa, Carmen; Perez, Eduardo; Perez, Roland, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 9, p. 764 - 769
  作者：Ochoa, Carmen、Perez, Eduardo、Perez, Roland、Suarez, Margarita、Ochoa, Estael、Rodriguez, Hortensia、Gomez Barrio, Alicia、Muclas, Susana、Jose Nogal, Juan、Martinez, Rafael A.

  DOI：——

  日期：——
• Synthesis and antimycobacterial activity of 3,5-disubstituted thiadiazine thiones
  作者：D. Katiyar、V.K. Tiwari、R.P. Tripathi、A. Srivastava、V. Chaturvedi、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0968-0896(03)00480-2

  日期：2003.10

  A series of 3,5-disubstituted thiadiazine thiones (4-24) have been synthesized by reaction of primary amines with carbon disulphide followed by cyclocondensation of the resulting intermediate with formaldehyde and primary amines or amino acids. The compounds were screened for antitubercular activity in vitro against Mycobacterium tuberculosis H37Rv. Three compounds 4, 12 and 18 showed antimycobacterial activity with MIC 12.5 mug/mL. Compound 4, was tested in vitro against five multidrug resistant (MDR) strains of M. tuberculosis and was found to be active. Compound 4 also exhibited activity in vivo. While all the mice died in the untreated group, the mean survival time (MST) of the compound treated mice was enhanced, 33% mice were surviving in treated group and the load of bacilli in the lung was considerably less in the compound treated group than in the untreated control group. (C) 2003 Elsevier Ltd. All rights reserved.
• A joint theoretical and experimental structural study of 5-carboxyethyl-3-(2′-furfurylmethyl) tetrahydro-2H-1,3,5-thiadiazine-2-thione
  作者：Rolando Pérez、Margarita Suárez、Estael Ochoa、Hortensia Rodrı́guez、Nazario Martı́n、Carlos Seoane、Héctor Novoa、Norbert Blaton、Oswald M Peeters、Camiel De Ranter

  DOI：10.1016/s0040-4020(01)00696-2

  日期：2001.8

  X-Ray analysis and semiempirical AM1 and ab initio HF/3-21G* and HF/6-31G* calculations reveal a favourable envelop conformation (A) for 3,5-disubstituted tetrahydro-2H-1,3,5-thiadiazines in which the N5 atom lies out of the main plane. NOE experiments show that this conformer (A) is also found in solution. (C) 2001 Elsevier Science Ltd. All rights reserved.