(吡咯烷-1-羰基硫代)硫代]乙酸 | 20069-28-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (吡咯烷-1-羰基硫代)硫代]乙酸
• 英文名称: S-(pyrrolidino-thiocarbonyl)-thioglycolic acid
• 英文别名: pyrrolinyldithiocarbamylacetic acid；(pyrrolidine-1-carbothioylsulfanyl)-acetic acid；Pyrrolidinodithiokohlensaeure-carboxymethylester；S-Carboxymethyl-pyrrolidin-N-carbodithioat；[(Pyrrolidin-1-ylcarbonothioyl)thio]acetic acid；2-(pyrrolidine-1-carbothioylsulfanyl)acetic acid
• CAS: 20069-28-7
• 化学式: C₇H₁₁NO₂S₂
• mdl: MFCD00583490
• 分子量: 205.302
• InChiKey: IHGSPAKPEOTIGY-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C(Solv: methanol (67-56-1))
• 沸点：
  353.6±44.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)
• 溶解度：
  26.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (吡咯烷-1-羰基硫代)硫代]乙酸 在 一水合肼 作用下， 生成 pyrrolidine-1-carbothioic acid hydrazide
  参考文献：
  名称：

  双吡唑啉：合成，表征和抗厌氧活性作为解组织变形虫的生长的抑制剂。

  摘要：

  在碱性条件下，用N-4取代的硫代氨基脲将查尔酮环化，导致形成新的化合物硫代氨基甲酰基双吡唑啉衍生物。通过UV，IR，1 H NMR，13 C NMR和ESI-MS光谱数据以及热重分析阐明了化合物的结构，并通过元素分析证实了其纯度。这些复合物的antiamoebic活性通过对微量稀释法评估HM1：IMSS的应变阿米巴并将结果与​​标准药物甲硝唑进行比较。结构-活性关系表明，在硫代氨基甲酰基上具有芳香取代基的化合物比具有环状基团的化合物更具活性。但是，从IC 50值可以清楚地看出，化合物15和20具有更高的活性，并且两者都显示出结构相似性，其中吸电子基团连接在苯环上。MTT分析表明所有化合物对人肾上皮细胞系无毒。

  DOI：

  10.1016/j.ejmech.2007.11.005
• 作为产物：
  描述：

  四氢吡咯 、 二硫化碳 、 sodium monochloroacetic acid 在 氢氧化钾 作用下， 生成 (吡咯烷-1-羰基硫代)硫代]乙酸
  参考文献：
  名称：

  双吡唑啉：合成，表征和抗厌氧活性作为解组织变形虫的生长的抑制剂。

  摘要：

  在碱性条件下，用N-4取代的硫代氨基脲将查尔酮环化，导致形成新的化合物硫代氨基甲酰基双吡唑啉衍生物。通过UV，IR，1 H NMR，13 C NMR和ESI-MS光谱数据以及热重分析阐明了化合物的结构，并通过元素分析证实了其纯度。这些复合物的antiamoebic活性通过对微量稀释法评估HM1：IMSS的应变阿米巴并将结果与​​标准药物甲硝唑进行比较。结构-活性关系表明，在硫代氨基甲酰基上具有芳香取代基的化合物比具有环状基团的化合物更具活性。但是，从IC 50值可以清楚地看出，化合物15和20具有更高的活性，并且两者都显示出结构相似性，其中吸电子基团连接在苯环上。MTT分析表明所有化合物对人肾上皮细胞系无毒。

  DOI：

  10.1016/j.ejmech.2007.11.005

文献信息

• Synthesis, Characterization and Biological Evaluation of Novel 1-N-Substituted Thiocarbomoyl-3-ferrocenyl-2-pyrazoline Derivatives
  作者：Humaira Parveen、Raedah Aiyed Suliman Alatawi、Salman Ahmad Khan、Mohammed Issa Al-Ahmdi、Sayeed Mukhtar、Amir Azam、Nadia H. Elsayed

  DOI：10.14233/ajchem.2016.19851

  日期：——

  Some novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. The results showed that most of the compounds exhibited promising activity (IC50 values in the range of 0.050-1.683 μM) than the reference drug metronidazole (IC50 = 1.78 μM). Active compounds were further screened for cytotoxicity against human embryonic kidney-293 (HEK-293) normal cell lines to ensure their toxic effect and the results revealed that active compounds were least toxic in the concentration range of 2.5-50 μM for 48 h and 2.5-25 μM for 72 h. At 100 μM for 48 h and at 50 μM for 72 h only four compounds 2c, 2h, 2k and 2l showed maximum viability and least cytotoxicity, respectively, concluding that all the screened compounds were least cytotoxic against human embryonic kidney-293 (HEK-293) normal cell lines in the concentration range of 2.5-50 and 2.5-25 μM.

  合成了一些新颖的1-N-取代硫代碳酰基-3-二茂铁基-2-吡唑啉衍生物，并评估了它们对Entamoeba histolytica的HM1:IMSS株的体外抗阿米巴活动。结果显示，多数化合物表现出比参考药物甲硝唑（IC50 = 1.78 μM）更有前景的活性（IC50值范围为0.050-1.683 μM）。进一步筛选活性化合物对人类胚胎肾-293（HEK-293）正常细胞系的细胞毒性，以确保其毒性效应，结果显示活性化合物在2.5-50 μM浓度范围内48小时和2.5-25 μM浓度范围内72小时内的毒性最小。在100 μM浓度下48小时和50 μM浓度下72小时，只有四种化合物2c、2h、2k和2l显示出最大的存活率和最小的细胞毒性，结论是所有筛选的化合物在2.5-50和2.5-25 μM浓度范围内对人类胚胎肾-293（HEK-293）正常细胞系的细胞毒性最小。
• Organotin esters of dithiocarbamylacetic acids
  作者：Seik Weng Ng、V.G. Kumar Das

  DOI：10.1016/0022-328x(91)86139-h

  日期：1991.5

  carboxylate-bridged structure with trans-C3SnO2 trigonal bipyramidal geometry at tin. The diorganotin dithiocarbamylacetates also adopt a bridged structure with a trans-C2SnO4 octahedral geometry at tin. The triorganotin esters dissociate into four-coordinate species in solution, as revelaed by NMR (1H and 13C) spectral data. The tri-cyclohexyltin esters, however, are four-coordinate monomers in the solid state and

  十二二和三有机锡的通式为R的dithiocarbamylacetic酸衍生物Ñ的Sn（O 2 CCH 2 š 2 CNR' 2）4- Ñ（R = Me中，Ñ卜，Ç己烷中，Ph; NR' 2 = NME 2制备NEt 2，N（CH 2）4，N（CH 2 CH 2）2 O；n＝ 3，2）。根据IR和Mössbauer光谱数据，将三甲基，三正丁基和三苯基锡衍生物分配为具有反式的羧酸桥结构-C 3 SnO 2在锡处的三角双锥几何形状。二有机锡二硫代氨基甲酸酯也采用在锡处具有反式-C 2 SnO 4八面体几何形状的桥联结构。NMR（1 H和13 C）光谱数据表明，三有机锡酸酯在溶液中解离为四配位物质。然而，三环己基锡酯是固态和溶液形式的四配位单体。三个distannoxanes，[（R“ 2的SnO 2 CCH 2小号2 CN-ME 2）O 2 ] 2（R” 2的Sn =卜在尝试由二有机锡二卤化物制
• Ensembling three multicomponent reactions for the synthesis of a novel category of pseudo-peptides containing dithiocarbamate and N,X-heterocylic groups
  作者：Maryam Khalesi、Azim Ziyaei Halimehjani、Max Franz、Marc Schmidtmann、Jürgen Martens

  DOI：10.1007/s00726-018-2661-0

  日期：2019.2

  Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS2 and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S

  连续多组分反应已用于合成仅在一个结构中带有二硫代氨基甲酸酯和N，X-杂环基团（X = S，O）的新型假肽。第一多组分反应包括使用胺或氨基酸，CS 2和亲电试剂合成二硫代氨基甲酸酯。第二个MCR是使用2-氯异丁醛，NaXH（X = S，O），酮和氨气合成Asinger亚胺的方法。最终的MCR是Ugi反应，可提供相应的三维伪肽。在该方案中使用了各种Asinger亚胺，羧酸和异氰酸酯，以高产率至优异产率提供了多种假肽。
• Synthesis of a new series of dithiocarbamate-linked peptidomimetics and their application in Ugi reactions
  作者：Azim Ziyaei Halimehjani、Mohammad Amin Ranjbari、Hamed Pasha Zanussi

  DOI：10.1039/c3ra44552f

  日期：——

  Novel peptidomimetics containing dithiocarbamate groups were synthesized via the Ugi reaction. Also, dithiocarbamates of natural amino acids were prepared and were used successfully in Ugi reactions to prepare novel peptidomimetics bearing amino acid and dithiocarbamate groups in a single structure. In addition the prepared dithiocarbamates based on amino acids are converted to the corresponding amides

  通过Ugi反应合成了含有二硫代氨基甲酸酯基团的新型拟肽。此外，还制备了天然氨基酸的二硫代氨基甲酸酯，并将其成功用于Ugi反应中，以制备具有单一结构的氨基酸和二硫代氨基甲酸酯基团的新型拟肽。另外，将基于氨基酸制备的二硫代氨基甲酸酯转化为相应的酰胺。
• Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines
  作者：Mohammad Abid、Abdul Roouf Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.032

  日期：2009.1

  Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, H-1 and C-13 NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis. (C) 2007 Elsevier Masson SAS. All rights reserved.