5-(2-thiophenylmethylidene)-2-thiohydantoin | 84071-21-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(2-thiophenylmethylidene)-2-thiohydantoin
• 英文别名: 4-thenylidene-2-thioxoimidazolidin-5-one；5-thiophen-2-ylmethylene-2-thioxo-imidazolidin-4-one；4-(2-Thienylmethylen)-2-thiohydantoin；2-Sulfanylidene-5-(thiophen-2-ylmethylidene)imidazolidin-4-one
• CAS: 84071-21-6
• 化学式: C₈H₆N₂OS₂
• 分子量: 210.28
• InChiKey: BHMMWVDJRGROOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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-(2-thiophenylmethylidene)-2-thiohydantoin 在 sodium hydroxide 、 氨 作用下， 以 甲醇 为溶剂， 反应 24.08h， 生成 3-D-glucopyranosyl-5-(2-thienylmethylene)hydantoin
  参考文献：
  名称：

  S-Glucosylated hydantoins as new antiviral agents

  摘要：

  S-Glycosylation took place on reaction of 5-alkylidene- and 5-arylidene-3-aryl-2-thiohydantoins with glycosyl halides under alkaline conditions. Bisglucosylation also took place when N-3 unsubstituted hydantoins were reacted. The bisglucosylated hydantoins produced N-3 glucosylated hydantoins on treatment with ammonia in methanol. In antiviral studies the most active compounds against both HSV-1 and HSV-2 were 5- (2-thienylmethylene) -3-phenyl-2-(2,3 4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin and 5-(2-thienylmethylene)-3-(4-chlorophenyl) -2- (2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) -2-thiohydantoin.

  DOI：

  10.1021/jm00027a009
• 作为产物：
  描述：

  2-硫代乙内酰脲 、 (2-噻吩亚甲基)甲烷-1,1-二甲腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到5-(2-thiophenylmethylidene)-2-thiohydantoin
  参考文献：
  名称：

  Girgis, Nabih Saddik; Elgemeie, Galal Eldin Hamza; Nawar, Galal Abdel Moein, Liebigs Annalen der Chemie, 1983, # 9, p. 1468 - 1475

  摘要：

  DOI：

文献信息

• [EN] AROMATIC IMIDAZOLIDINONE DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASES OF BACTERIAL NATURE<br/>[FR] DÉRIVÉS D'IMIDAZOLIDINONES AROMATIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES DE NATURE BACTÉRIENNE
  申请人：UNIV JAGIELLONSKI

  公开号：WO2013151450A1

  公开（公告）日：2013-10-10

  The invention introduces new derivatives of aromatic imidazolidinones, which fall within the scope of the general formula I and their pharmaceutical forms of suitable additive salts with acids, wherein R1 and R2 are as defined herein, in particular for the prevention or treatment of diseases of bacterial nature. The invention further introduces the use of compounds according to the invention for the manufacture of a medication useful for the treatment of various conditions as described above.

  该发明介绍了芳香基咪唑烷酮的新衍生物，其属于一般式I范围内，以及它们与酸适当添加盐的药用形式，其中R1和R2如本文所定义，特别用于预防或治疗细菌性疾病。该发明进一步介绍了根据该发明的化合物用于制造用于治疗上述各种疾病的药物的用途。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• 10.1016/j.bioorg.2024.107471
  作者：Sheta, Yasmin S.、Sarg, Marwa T.、Abdulrahman, Fatma G.、Nossier, Eman S.、Husseiny, Ebtehal M.

  DOI：10.1016/j.bioorg.2024.107471

  日期：——

  variation, substituents variation, and ring fusion, two series of 2-(alkylthio)-5-(arylidene/heteroarylidene)imidazolones and imidazo[1,2-]thieno[2,3-]pyrimidines were designed and prepared as dual potential Chk1 and Chk2 inhibitors. The newly synthesized hybrids were screened in NCI 60 cell line panel where the most active derivatives , and were further estimated for their five dose antiproliferative

  应用包括环变异、取代基变异和环融合在内的各种药物设计策略，设计了两个系列的2-(烷硫基)-5-(亚芳基/亚杂芳基)咪唑啉酮和咪唑并[1,2-]噻吩并[2,3-]嘧啶。设计和制备为双重潜在的 Chk1 和 Chk2 抑制剂。新合成的杂交体在NCI 60细胞系中进行了筛选，其中衍生物最活跃，并进一步评估了它们对最敏感肿瘤细胞（包括乳腺MCF-7和MDA-MB-468以及非小细胞）的五剂量抗增殖活性。肺癌EKVX以及正常WI-38细胞。值得注意的是，增加咪唑酮支架 C-2 上硫醇部分的碳链可提高细胞毒性活性。因此，含有 S-丁基片段的化合物 和 ，对测试细胞表现出最强的抗增殖活性，并对它们显示出极强的选择性。此外，含有咪唑并噻吩并嘧啶核心的化合物对所检测的细胞具有显着的细胞毒活性和选择性。通过评估最活跃的细胞毒性类似物对 Chk1 和 Chk2 的抑制活性，对它们进行了机制研究。结果显示，对 Chk1
• Abdelaziz, Mahfouz A.; Moharram, H. H.; Essawy, Samy A., Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 48, # 1-4, p. 269 - 273
  作者：Abdelaziz, Mahfouz A.、Moharram, H. H.、Essawy, Samy A.、Mohamed, A. A.

  DOI：——

  日期：——
• Girgis, Nabih Saddik; Elgemeie, Galal Eldin Hamza; Nawar, Galal Abdel Moein, Liebigs Annalen der Chemie, 1983, # 9, p. 1468 - 1475
  作者：Girgis, Nabih Saddik、Elgemeie, Galal Eldin Hamza、Nawar, Galal Abdel Moein、Elnagdi, Mohamed Hilmy

  DOI：——

  日期：——