5-(2-噻吩基亚甲基)-2-硫酮噻唑烷-4-酮 | 6319-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-(2-噻吩基亚甲基)-2-硫酮噻唑烷-4-酮
• 英文名称: 5-thiophen-2-ylmethylenerhodanine
• 英文别名: 5-(thiophen-2-ylmethylene)-2-thioxothiazolidin-4-one；5-(2-thienylmethylene)-2-thioxo-1,3-thiazolidin-4-one；(Thiophenyliden-3)-5 rhodanin；5-(2'-thiophenemethylene)rhodamine；5-[2]thienylmethylene-2-thioxo-thiazolidin-4-one；5-[2]Thienylmethylen-2-thioxo-thiazolidin-4-on；2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-4-one
• CAS: 6319-47-7
• 化学式: C₈H₅NOS₃
• mdl: MFCD00225207
• 分子量: 227.332
• InChiKey: XLYORYAUKZCBPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  115
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-噻吩基亚甲基)-2-硫酮噻唑烷-4-酮 在 吡啶 作用下， 反应 8.0h， 生成 3-[3-Oxo-3H-isobenzofuran-(1E)-ylidenemethyl]-5-[1-thiophen-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-噻吩甲醛 、 罗丹宁 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到5-(2-噻吩基亚甲基)-2-硫酮噻唑烷-4-酮
  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

• Synthesis, biological evaluation, and molecular docking study of thiophene‐, piperazine‐, and thiazolidinone‐based hybrids as potential antimicrobial agents
  作者：Nisheeth C. Desai、Yogesh M. Rupala、Ashvinkumar G. Khasiya、Keyur N. Shah、Unnat P. Pandit、Vijay M. Khedkar

  DOI：10.1002/jhet.4366

  日期：2022.1

  Antibiotic resistance in bacteria exacerbates the issue of antimicrobial resistance. Bacteria that cause common or serious infections have evolved resistance to every new antibiotic that has been introduced into the market, to varying degrees, over several decades. Faced with this reality, one of society's most urgent needs is for new antimicrobial drugs with novel mechanisms of action. With this objective

  细菌中的抗生素耐药性加剧了抗菌素耐药性问题。几十年来，导致常见或严重感染的细菌已经对每种引入市场的新抗生素产生了不同程度的耐药性。面对这一现实，社会最迫切的需求之一是寻找具有新作用机制的新型抗菌药物。为了这个目标，我们在此描述了一组新型化合物的开发，包括基于哌嗪和噻吩的噻唑烷酮(5a-i)和噻吩-噻唑烷酮(6a-i)。化合物(5a-i)和(6a-i)开发、合成并测试了它们的抗菌活性，并在各种分析技术的帮助下阐明了它们的结构。化合物5a和5d对铜绿假单胞菌表现出优异的抗菌功效，MIC 为 50 μg/ml，而化合物6c和6e分别对金黄色葡萄球菌和大肠杆菌表现出相似的效力。化合物5e和6i对白色念珠菌的抗真菌功效非常显着（MIC = 50 μg/ml）。唯一具有优异抗真菌功效的化合物黑曲霉是化合物5e (MIC = 50 μg/ml)。化学-硅-生物学方法可以为这种新型杂交支架在开发有前景的抗菌剂方面的潜力提供有价值的见解。
• N-Glucopyranosyl-5-aralkylidenerhodanines: Synthesis and Antibacterial and Antiviral Activities
  作者：William O. Foye、Phichai Tovivich

  DOI：10.1002/jps.2600661126

  日期：1977.11

  N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-beta-D-Glucopyranosyl-5-(4-nitrobenzylidene) rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.

  合成了一系列的N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-5-芳烷基亚乙基金丹宁，并且除去了乙酰基基团，得到了N-β-D-吡喃葡萄糖基-5-芳烷基亚芳基但不通过酸水解裂解若丹宁环。在甲醇中用氨水进行碱水解会裂解为N-葡萄糖基硫脲，为N-糖苷的形成提供了证据。许多若丹宁衍生物，特别是在芳族环中具有硝基或氯基的那些，均显示出抗菌活性。N-β-D-Glucopyranosyl-5-（4-硝基亚苄基）若丹宁通过抑制病毒RNA合成表现出抗病毒活性。几种罗丹宁对血糖水平也有一定影响。
• Methyl- and phenylmercury(II) complexes of 5-(4′-dimethylaminobenzylidene)rhodanine (HDABRd) and 5-(2′-thiophenomethylene)rhodanine (HTRd). The crystal and molecular structure of [HgPh(DABRd)] and [HgMe(TRd)]
  作者：José S Casas、Eduardo E Castellano、Alejandro Macı́as、Nuria Playá、Agustı́n Sánchez、José Sordo、José M Varela、Ezequiel M Vázquez-López

  DOI：10.1016/s0277-5387(01)00752-5

  日期：2001.6

  )rhodanine (HDABRd) and 5-(2′-thiophenomethylene)rhodanine (HTRd) with methyl- and phenylmercury(II) acetate yielded [HgR(DABRd)] and [HgR(TRd)] (R=Me, Ph), respectively. These complexes were characterized and studied by IR and NMR (1H, 13C1H} and 199Hg) spectroscopy, and X-ray diffractometry, respectively. In both structures the rhodanine ligand coordinates to the mercury atom via its N(3) atom,

  5-（4'-二甲基氨基亚苄基）罗丹宁（HDABRd）和5-（2'-噻吩亚甲基）罗丹宁（HTRd）与乙酸甲基和苯基汞（II）的反应生成[HgR（DABRd）]和[HgR（TRd） ]（R = Me，Ph）。分别通过IR和NMR（1 H，13 C 1 H}和199 Hg）光谱和X射线衍射法对这些配合物进行了表征和研究。在两个结构中，若丹宁配体均通过其N（3）原子与汞原子配位，并且HgC（13）和HgN（3）几乎共线。汞原子还形成分子内和分子间的次级键。尤其是，Hg⋯S键使平行于b的锯齿形链中的[HgPh（DABRd）]分子缔合 Hg⋯O键连接着中心对称二聚体中的[HgMe（TRd）]分子。
• Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors
  作者：Si-Ning Li、Yun-Yun Xu、Jia-Yu Gao、Hong-ran Yin、Shi-Lei Zhang、Huan-Qiu Li

  DOI：10.1016/j.bmc.2015.04.065

  日期：2015.7

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
  作者：Sakshi Shah、Baldev Singh

  DOI：10.1016/j.bmcl.2012.07.049

  日期：2012.9

  An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure. (C) 2012 Elsevier Ltd. All rights reserved.