ethane-1,2-dithiosemicarbazide | 1728-65-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethane-1,2-dithiosemicarbazide
• 英文别名: 1-Amino-3-[2-(aminocarbamothioylamino)ethyl]thiourea
• CAS: 1728-65-0
• 化学式: C₄H₁₂N₆S₂
• 分子量: 208.311
• InChiKey: OCODKEGXDNJQND-UHFFFAOYSA-N

物化性质

• 熔点：
  221 °C (decomp)
• 沸点：
  383.3±52.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二茂铁甲醛 、 ethane-1,2-dithiosemicarbazide 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以98%的产率得到
  参考文献：
  名称：

  Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds

  摘要：

  A series of mono- and multimeric 4-amino-7-chloroquinoline and ferrocenyl thioureas have been prepared by the reaction of a 7-chloroquinoline methyl ester and a ferrocenylimine methyl ester with various amines. These compounds were characterized using standard spectroscopic and analytical techniques. The compounds were evaluated against the NF54 (CQ-sensitive) and Dd2 (CQ-resistant) strains of Plasmodium falciparum. The quinoline compounds show enhanced activity compared to the ferrocene compounds against this parasite. Compound 5 displays the most promising activity against the NF54 strain. Compounds 5 and 6 are effective at inhibiting beta-hematin formation perhaps due to an increased number of quinoline moieties. The trimeric (12) and tetrameric (13) ferrocenyl compounds also inhibit beta-hematin formation, albeit to a lesser degree compared to the quinoline thioureas. The compounds were also screened against the G3 strain of Trichomonas vaginalis and here the ferrocenecontaining compounds show a slightly higher parasite growth inhibition compared to the quinoline thioureas. The quinoline compounds were also found to be more cytotoxic compared to the ferrocenyl compounds. Compound 6 displays good cytotoxicity against WHCO1 oesophageal cancer cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.004
• 作为产物：
  描述：

  乙烯二(亚氨基硫代甲酰硫代)二乙酸 在 盐酸 、 肼 作用下， 反应 2.0h， 以3.32 g的产率得到ethane-1,2-dithiosemicarbazide
  参考文献：
  名称：

  锌和铜的双（硫代半氨基甲酸酯）配合物的环外官能化：单体和二聚体物种的合成。

  摘要：

  本文报道了使用1,3-或1,4-苯二胺或1,3-或1,4-苯二醛作为连接基团的具有刚性芳族连接基的双金属硫代氨基脲锌配合物的合成。非刚性脂族二胺和二醛也用于连接锌螯合单元。具有侧基NHNH（2）的双（硫代半脲）与单醛或酮的反应产生了一系列带有带有一定取代基的胞外亚胺基的单体配合物。可以将锌络合物定量快速地金属化为相应的铜络合物，并且该途径或与游离配体的直接反应可用于用（64）Cu放射性标记单体。

  DOI：

  10.1039/b705087a

文献信息

• Synthesis of new antimicrobials. V. Synthesis of alkylenebis-(thiosemicarbazides) and their related compounds.
  作者：TAKAHIRO YABUUCHI、MASAKATU HISAKI、RYUICHI KIMURA

  DOI：10.1248/cpb.23.668

  日期：——

  Several kinds of alkylenebis (thiosemicarbazide) and alkylenebis (bithiourea) derivatives were synthesized in order to examine their antimicrobial activity. 1, 1'-Dibenzylidene-4, 4'-alkylene-bis (thiosemicarbazides) were prepared from 4, 4'-alkylene-bis (thiosemicarbazides) and arylaldehydes, and 1, 1'-diaroyl-4, 4'-hexamethylene-bis (thiosemicarbazides) were prepared by the reaction of 4', 4'-hexamethylene-bis (thiosemicarbazide) with aroyl chlorides. 1, 1'-Dialkyl- or diaryl-6, 6'-alkylene-bis (bithioureas) were synthesized from 4, 4'-alkylene-bis (thiosemicarbazides) and alkyl or aryl isothiocyanates. N, N'-Hexamethylene-bis [2-amino-5-(2-methoxyphenyl) thiadiazole] was prepared by the ring closure of 1, 1'-bis (2-methoxybenzylidene) -4, 4'-hexamethylene-bis (thiosemicarbazide).

  为了检测其抗微生物活性，合成了几种烷基亚甲基双（硫脲素）和烷基亚甲基双（二硫脲）衍生物。1, 1'-二苄叉-4, 4'-烷基亚甲基双（硫脲素）是通过4, 4'-烷基亚甲基双（硫脲素）和芳醛的反应制备的，而1, 1'-二芳酰-4, 4'-六亚甲基双（硫脲素）则是通过4, 4'-六亚甲基双（硫脲素）与芳酰氯的反应制备的。1, 1'-二烷基或二芳基-6, 6'-烷基亚甲基双（二硫脲）是通过4, 4'-烷基亚甲基双（硫脲素）与烷基或芳基异硫氰酸酯的反应合成的。N, N'-六亚甲基-双[2-氨基-5-(2-甲氧基苯基)噻二唑]是通过1, 1'-双(2-甲氧基苄叉)-4, 4'-六亚甲基双（硫脲素）的环合反应制备的。
• The synthesis and properties of some dithiosemicarbazones
  作者：D. M. Wiles、B. A. Gingras、T. Suprunchuk

  DOI：10.1139/v67-282

  日期：1967.8.1

  A series of new compounds has been prepared by reacting aliphatic and aromatic aldehydes with ethylene dithiosemicarbazide. The nature of these new dithiosemicarbazones has been deduced from their infrared spectra, from the products of the ferric chloride induced oxidation of two of them, and from the formation of 1:1 copper complexes of several of them. Since the copper complexes are paramagnetic, the copper must be present in the cupric oxidation state. A structure has therefore been proposed for the complexes which involves bonding between copper and both thiocarbonyl groups in the dithiosemicarbazone molecule.Several of the compounds prepared in this work exhibit an antifungal action against the cellulolytic microorganism Chaetomium globosum.

  一系列新化合物已通过将脂肪族和芳香族醛与乙二硫代半脲反应而制备出来。这些新的二硫代半脲的性质已从它们的红外光谱、两种化合物在三氯化铁诱导氧化后的产物以及其中几种的1:1铜配合物的形成中推断出来。由于铜配合物是顺磁性的，所以铜必须存在于铜氧化态。因此，已经提出了一种结构，其中涉及铜与二硫代半脲分子中的两个硫代羰基之间的键合。在这项工作中制备的几种化合物对纤维素分解微生物球孢毛霉具有抗真菌作用。
• Sen,A.B.; Gupta,S.K., Journal of the Indian Chemical Society, 1962, vol. 39, p. 628 - 634
  作者：Sen,A.B.、Gupta,S.K.

  DOI：——

  日期：——
• Some transformations of ?,?-bis(1,3-thiazan-2-thion-4-on-3-yl)alkanes
  作者：B. S. Zimenkovskii、N. M. Turkevich

  DOI：10.1007/bf00488907

  日期：1977.8
• Zimenkovskii,B.S., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 1989 - 1990
  作者：Zimenkovskii,B.S.

  DOI：——

  日期：——