5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one | 53428-07-2

• 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: 5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one
• 英文别名: 5-Pyrrol-2-ylmethylen-2-thioxo-thiazolidin-4-on；5-(1H-pyrrol-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 53428-07-2
• 化学式: C₈H₆N₂OS₂
• 分子量: 210.28
• InChiKey: RRJVVJRJMYKPGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one 在 吡啶 作用下， 反应 8.0h， 生成 3-[3-Oxo-3H-isobenzofuran-(1E)-ylidenemethyl]-5-[1-(1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  Donia, Shaffy Galal, Pakistan Journal of Scientific and Industrial Research, 1992, vol. 35, # 12, p. 489 - 491

  摘要：

  DOI：
• 作为产物：
  描述：

  2-吡咯甲醛 、 罗丹宁 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以72%的产率得到5-pyrrol-2-ylmethylene-2-thioxo-thiazolidin-4-one
  参考文献：
  名称：

  罗丹宁及其相关杂环化合物对金黄色葡萄球菌和鲍曼不动杆菌的合成及抗菌评价

  摘要：

  抗菌素耐药性是现代医学面临的严峻挑战。除了造成高昂的经济负担外，耐多药感染也是高发病率和高死亡率的直接原因。尽管目前有许多抗生素可用于治疗由 ESKAPE 微生物引起的感染，但越来越多的细菌菌株对这些药物产生了耐药性。普遍的情况迫切需要开发新的抗菌药物来治疗由耐多药微生物引起的感染。罗丹宁和结构相关的 5 元杂环具有广泛的药理活性。许多这些衍生物已显示出对各种微生物的良好有效抑制作用。据报道，它们会改变 DNA 促旋酶 B、金属-β-内酰胺酶、青霉素结合蛋白 (PBP)、Mur 连接酶、RNA 聚合酶、烯酰 ACP 还原酶、1-脱氧-d-木酮糖-5-磷酸还原异构酶。等对细菌的生长、生存和复制至关重要。在这项研究中，我们生成了罗丹宁和相关 5 元杂环衍生物的文库，并针对一组病原体对其进行了筛选。在所有化合物中，2a - i、3a - b、3g、4、6b - c、6e、6g、12a - b和14b

  DOI：

  10.1002/cbdv.202200213

文献信息

• Ponomarew; Ditschkowa, Uchenye Zapiski Saratovskogo Gosudarstvennogo Universiteta, 1955, vol. 42, p. 45,48
  作者：Ponomarew、Ditschkowa

  DOI：——

  日期：——
• Synthesis, molecular structure investigations and antimicrobial activity of 2-thioxothiazolidin-4-one derivatives
  作者：Assem Barakat、Hany J. Al-Najjar、Abdullah Mohammed Al-Majid、Saied M. Soliman、Yahia Nasser Mabkhot、Mohamed H.M. Al-Agamy、Hazem A. Ghabbour、Hoong-Kun Fun

  DOI：10.1016/j.molstruc.2014.10.038

  日期：2015.2

  A variety of 2-thioxothiazolidin-4-one derivatives were prepared and their in vitro antimicrobial activities were studied. Most of these compounds showed significant antibacterial activity specifically against Gram-positive bacteria, among which compounds 4a,e,g, 5b,e,g,h and 6f exhibit high levels of antimicrobial activity against Bacillus subtilis ATCC 10400 with Minimum Inhibitory Concentration (MIC) value of 16 mu g/mL. All compounds have antifungal activity against Candida albicans. Unfortunately, however, none of the compounds were active against Gram-negative bacteria. The chemical structure of 3 was confirmed by X-ray single crystal diffraction technique. DFT calculations of 3 have been performed on the free C10H7Cl2NO2S2, 3a and the H-bonded complex, C10H7Cl2NO2S2 center dot H2O, 3b to explore the effect of the H-bonding interactions on the geometric and electronic properties of the studied systems. A small increase in bond length was observed in the C12-O6 due to the H-bonding interactions between 3a and water molecule. MEP study has been used to recognize the most reactive sites towards electrophilic and nucleophilic attacks as well as the possible sites for the H-bonding interactions. The TD-DFT calculations have been used to predict theoretically the electronic spectra of the studied compound. The most intense transition band is predicted at 283.9 nm due to the HOMO-2/HOMO-1 to LUMO transitions. NBO analyses were carried out to investigate the stabilization energy of the various intramolecular charge transfer interactions within the studied molecules. (C) 2014 Elsevier B.V. All rights reserved.
• The Reaction of Pyrrolealdehyde with Rhodanine and Hydantoin¹
  作者：Werner Herz、Karl Dittmer

  DOI：10.1021/ja01182a021

  日期：1948.2
• Donia, Shaffy Galal, Pakistan Journal of Scientific and Industrial Research, 1992, vol. 35, # 12, p. 489 - 491
  作者：Donia, Shaffy Galal

  DOI：——

  日期：——
• Synthesis and Antibacterial Evaluation of Rhodanine and Its Related Heterocyclic Compounds against <i>S. aureus</i> and <i>A. baumannii</i>
  作者：Ravikumar Akunuri、Tanveer Unnissa、Grace Kaul、Abdul Akhir、Deepanshi Saxena、Mohmadd Wajidali、Vaishnavi Veerareddy、Venkata Madhavi Yaddanapudi、Sidharth Chopra、Srinivas Nanduri

  DOI：10.1002/cbdv.202200213

  日期：2022.7

  library of Rhodanine and related 5 membered heterocyclic derivatives and screened them against a panel of pathogens. Among all the compounds, 2a–i, 3a–b, 3g, 4, 6b–c, 6e, 6g, 12a–b and 14b–c have demonstrated good to moderate inhibition against S. aureus (MIC 0.125–8 μg/mL). Further, compound 17b demonstrated moderate activity against A. baumannii (MIC 8 μg/mL). In addition, compounds 2a, 2e, 4, 6c, 6g and

  抗菌素耐药性是现代医学面临的严峻挑战。除了造成高昂的经济负担外，耐多药感染也是高发病率和高死亡率的直接原因。尽管目前有许多抗生素可用于治疗由 ESKAPE 微生物引起的感染，但越来越多的细菌菌株对这些药物产生了耐药性。普遍的情况迫切需要开发新的抗菌药物来治疗由耐多药微生物引起的感染。罗丹宁和结构相关的 5 元杂环具有广泛的药理活性。许多这些衍生物已显示出对各种微生物的良好有效抑制作用。据报道，它们会改变 DNA 促旋酶 B、金属-β-内酰胺酶、青霉素结合蛋白 (PBP)、Mur 连接酶、RNA 聚合酶、烯酰 ACP 还原酶、1-脱氧-d-木酮糖-5-磷酸还原异构酶。等对细菌的生长、生存和复制至关重要。在这项研究中，我们生成了罗丹宁和相关 5 元杂环衍生物的文库，并针对一组病原体对其进行了筛选。在所有化合物中，2a - i、3a - b、3g、4、6b - c、6e、6g、12a - b和14b