1,1'-thiocarbonyldiimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1'-thiocarbonyldiimidazole
• 英文别名: Imidazol-1-yl(pyrazol-1-yl)methanethione；imidazol-1-yl(pyrazol-1-yl)methanethione
• 化学式: C₇H₆N₄S
• 分子量: 178.217
• InChiKey: RSTILRMJWQTTCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1'-thiocarbonyldiimidazole 、 以 乙腈 为溶剂， 以75 mg的产率得到methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-(1'-(2',3',4',6'-tetra-O-benzyl-1'deoxy-α-D-mannopyranosyl)(oxythiocarbonylimidazolyl)methyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

  DOI：

  10.1021/jo020339z

文献信息

• Diverted Total Synthesis and Biological Evaluation of Gambierol Analogues: Elucidation of Crucial Structural Elements for Potent Toxicity
  作者：Haruhiko Fuwa、Noriko Kainuma、Kazuo Tachibana、Chihiro Tsukano、Masayuki Satake、Makoto Sasaki

  DOI：10.1002/chem.200400355

  日期：2004.10.4

  gambierol analogues have been prepared from an advanced intermediate of our total synthesis of gambierol and investigated for their toxicity against mice, thus providing the first systematic structure-activity relationships (SAR) of this polycyclic ether class of marine toxin. The SAR studies described herein clearly indicate that 1) the C28=C29 double bond within the H ring and the unsaturated side chain

  Gambierol是一种多环醚毒素，已从海洋鞭毛鞭毛藻Gambierdiscus toxicus中分离出来。从我们的甘菊醇总合成的高级中间体中制备了一系列甘菊醇类似物，并研究了其对小鼠的毒性，从而提供了该多环醚类海洋毒素的第一个系统结构-活性关系（SAR）。本文所述的SAR研究清楚地表明：1）H环内的C28 = C29双键和不饱和侧链是发挥强大生物活性所需的关键结构元素，以及2）C1和C6羟基，C30甲基C37 = C38双键对小鼠的神经毒性程度影响很小。
• NOVELCROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC CONJUGATES, AND SYNTHETIC METHODS THEREOF
  申请人：CellMosaic, Inc.

  公开号：US20140206903A1

  公开（公告）日：2014-07-24

  The invention provides novel chemical entities based on sugar alcohols. These new chemical entities are biocompatible and biodegradable. The molecules can be made in a single and pure form. The molecular weights of these molecules range from small (<1000 Da) to large (1000-120,000 Da). The sugar alcohol-based molecules can have functional groups throughout the molecule for crosslinking compounds, such as the preparation of antibody-drug conjugates, or to facilitate the delivery of therapeutic proteins, peptides, siRNA, and chemotherapeutic drugs. Also provided are new conjugate entities prepared through sugar alcohol molecules. Methods of synthesizing sugar alcohol-based molecules and conjugates are also within the scope of the invention.

  本发明提供了基于糖醇的新型化合物。这些新型化合物具有生物相容性和生物可降解性。这些分子可以以单一纯形式制备。这些分子的分子量范围从小分子（<1000 Da）到大分子（1000-120,000 Da）。基于糖醇的分子可以在整个分子中具有功能性基团，用于交联化合物，例如制备抗体药物偶联物，或促进治疗性蛋白质、肽、siRNA和化学治疗药物的传递。还提供了通过糖醇分子制备的新型偶联实体。本发明还涉及制备基于糖醇的分子和偶联物的方法。
• Novel 1,2,3,4-tetrahydroisoquinoline-based Schiff bases as laccase inhibitors: Synthesis and biological activity, 3D-QSAR, and molecular docking studies
  作者：Huan Xu、Xingxing Lu、Tengda Sun、Qi He、Yue Qi、Yufan Lin、Xinling Yang、Li Zhang、Yun Ling、Xiaoming Zhang

  DOI：10.1016/j.molstruc.2023.135526

  日期：2023.8

  Laccase is considered a potential target in the field of agricultural fungicides. To promote the discovery and development of compounds with laccase inhibitory activity, herein, taking reported laccase inhibitor 4-chlorocinnamaldehyde thiosemicarbazide (PMDD-5Y) as the lead compound, two series of 29 novel Schiff-base compounds were designed and synthesized by introducing natural structural unit 1

  漆酶被认为是农业杀菌剂领域的一个潜在目标。为促进具有漆酶抑制活性的化合物的发现和开发，本文以报道的漆酶抑制剂4-氯肉桂醛氨基硫脲(PMDD-5Y)为先导化合物，通过引入天然结构设计合成了两个系列的29个新型席夫碱化合物。单元1,2,3,4-四氢异喹啉为首次。所有合成的化合物在体外对几种植物病原真菌均具有良好的抗真菌活性。其中化合物4k对Valsa mali (EC 50  = 5.37 µg/mL)、立枯丝核菌( Rhizoctonia solani (EC 50 = 3.51 µg/mL) 和漆酶 (IC 50  = 0.047 mmol/L)，因此，可能成为靶向漆酶的新型化学杀菌剂的有前途的候选者。此外，利用三维定量构效关系、分子对接和密度泛函理论计算研究了化合物的构效关系。实验结果初步表明，作为带正电区域的氮原子上的活性氢可以与漆酶靶点形成关键相互作用。这可能是影响生物活性的关键因素。
• Synthesis of an 11-unsubstituted analogue of (±)-huperzine A
  作者：Pelayo Camps、Joan Contreras、Jordi Morral、Diego Muñoz-Torrero、Mercè Font-Bardia、Xavier Solans

  DOI：10.1016/s0040-4020(99)00434-2

  日期：1999.7

  The synthesis of a new analogue of (+/-)-huperzine A lacking the ethylidene appendage at position ii has been accomplished. The key steps of the synthesis were: a) the reduction of the keto function of the known methyl 7.7-ethylenedioxy-3-methyl-9-oxobicyclo[3.3.1]non-3-ene-1 -carboxylate into a methylene group by reduction to a mixture of stereoisomeric alcohols followed by alcohol-deoxygenation through a Barton-McCombie procedure and b) the elaboration of the pyridone ring in a late stage of the synthesis by reaction of a pyrrolidine enamine with propiolamide, which gave a mixture of regioisomeric pyridone derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
• NOVEL CROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC BIOCONJUGATES, AND SYNTHETIC METHODS THEREOF
  申请人：CellMosaic, Inc.

  公开号：US20170065726A1

  公开（公告）日：2017-03-09

  The invention provides novel chemical entities based on sugar alcohols. These new chemical entities are biocompatible and biodegradable. The molecules can be made in a single and pure form. The molecular weights of these molecules range from small (<1000 Da) to large (1000-120,000 Da). The sugar alcohol-based molecules can have functional groups throughout the molecule for crosslinking compounds, such as the preparation of antibody-drug conjugates, or to facilitate the delivery of therapeutic proteins, peptides, siRNA, and chemotherapeutic drugs. Also provided are new conjugate entities prepared through sugar alcohol molecules. Methods of synthesizing sugar alcohol-based molecules and conjugates are also within the scope of the invention.