thieno[2,3-d][1,2,3]thiadiazole-6-carboxylic acid | 192878-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: thieno[2,3-d][1,2,3]thiadiazole-6-carboxylic acid
• 英文别名: thieno[2,3-d]1,2,3-thiadiazole-6-carboxylic acid；thieno[2,3-d]thiadiazole-6-carboxylic acid
• CAS: 192878-30-1
• 化学式: C₅H₂N₂O₂S₂
• mdl: MFCD05256444
• 分子量: 186.215
• InChiKey: FDZNFTUGBZLIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 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：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thieno[2,3-d][1,2,3]thiadiazole-6-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-(1,1-dimethylethyl)-thieno<2,3-d><1,2,3>thiadiazole-6-carboxamide
  参考文献：
  名称：

  Stanetty, Peter; Jaksits, Marion; Mihovilovic, Marko D., Advanced Synthesis and Catalysis, 1999, vol. 341, # 4, p. 391 - 394

  摘要：

  DOI：
• 作为产物：
  描述：

  衣康酸 在 劳森试剂 、 sodium hydroxide 、 氯化亚砜 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 thieno[2,3-d][1,2,3]thiadiazole-6-carboxylic acid
  参考文献：
  名称：

  A new type of plant activator: synthesis of thieno[2,3-d ][1,2,3]thiadiazole-6-carboxylic acid derivatives via Hurd–Mori cyclization

  摘要：

  我们提出了一种以廉价且容易获得的亚甲基丁二酸和硫代乙酸为起始原料的标题化合物的简短而有效的合成方法。优化的序列允许通过几个步骤大规模制备这种新型植物活化剂。邻位锂化用于将取代基引入5-位。建议对 Hurd–Mori 反应的反应机制进行修改来解释意外的芳构化。

  DOI：

  10.1039/a708375k

文献信息

• Synthesis, Identification, and Structure–Activity Relationship Analysis of GATA4 and NKX2-5 Protein–Protein Interaction Modulators
  作者：Mikael Jumppanen、Sini M. Kinnunen、Mika J. Välimäki、Virpi Talman、Samuli Auno、Tanja Bruun、Gustav Boije af Gennäs、Henri Xhaard、Ingo B. Aumüller、Heikki Ruskoaho、Jari Yli-Kauhaluoma

  DOI：10.1021/acs.jmedchem.9b01086

  日期：2019.9.12

  cytotoxicity. The structure-activity relationship (SAR) analysis revealed that the aromatic isoxazole substituent in the southern part regulates the inhibition of GATA4-NKX2-5 transcriptional synergy. Moreover, inhibition of GATA4 transcriptional activity correlated with the reduced cell viability. In summary, comprehensive SAR analysis accompanied by data analysis successfully identified potent and selective

  转录因子GATA4和NKX2-5直接相互作用并协同激活几种心脏基因和牵张诱导的心肌肥大。以前，我们将苯基异恶唑羧酰胺1确定为命中化合物，该化合物可抑制GATA4-NKX2-5转录协同作用。在此，通过合成和表征220个衍生物和与结构相关的化合物，探索了1分子结构周围的化学空间。除了协同转录激活，还评估了所选化合物对GATA4和NKX2-5转录活性的影响以及潜在的细胞毒性。结构-活性关系（SAR）分析表明，南部的芳族异恶唑取代基可调节对GATA4-NKX2-5转录协同的抑制作用。而且，对GATA4转录活性的抑制与细胞活力的降低有关。总之，综合的SAR分析和数据分析成功地确定了GATA4-NKX2-5转录协同作用的有效和选择性抑制剂，并揭示了对其重要的结构特征。
• Microbicides
  申请人：Novartis Finance Corporation

  公开号：US05814629A1

  公开（公告）日：1998-09-29

  The invention relates to novel microbicidal and plant-immunising compounds of formula I ##STR1## wherein: X is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, SR.sub.8, N(R.sub.9)R.sub.10, CH.sub.2 OH, CHO or COOR.sub.8 ; R.sub.8 to R.sub.10 are hydrogen, C.sub.1 -C.sub.4 alkyl, benzyl, C.sub.1 -C.sub.4 acyl or benzoyl; Z is hydrogen, halogen, or a methyl group that is unsubstituted or to which from 1 to 3 unsubstituted or substituted hetero atoms O, S and/or N are bonded; in free form or in the form of salts. They can be used in crop protection for controlling and preventing disease infestation.

  本发明涉及一种新型杀菌和植物免疫化合物，其化学式为I ##STR1## 其中：X是氢、卤素、C.sub.1-C.sub.4烷基、SR.sub.8、N（R.sub.9）R.sub.10、CH.sub.2OH、CHO或COOR.sub.8；R.sub.8到R.sub.10是氢、C.sub.1-C.sub.4烷基、苯甲基、C.sub.1-C.sub.4酰基或苯甲酰基；Z是氢、卤素或一个未取代或与1到3个未取代或取代的杂原子O、S和/或N结合的甲基基团；以自由形式或盐的形式存在。它们可用于作物保护，控制和预防疾病侵染。
• 噻吩并噻二唑衍生物及其作为植物抗病激活 剂的应用
  申请人：华东理工大学

  公开号：CN103509039B

  公开（公告）日：2017-07-28

  发明涉及式I所示的噻吩并噻二唑系列衍生物及其作为植物抗病激活剂的应用。
• Novel plant activators with thieno[2,3-d]-1,2,3-thiadiazole-6-carboxylate scaffold: Synthesis and bioactivity
  作者：Qing-Shan Du、Yan-Xia Shi、Peng-Fei Li、Zhen-Jiang Zhao、Wei-Ping Zhu、Xu-Hong Qian、Bao-Ju Li、Yu-Fang Xu

  DOI：10.1016/j.cclet.2013.07.003

  日期：2013.11

  The 1,2,3-thiadiazole-carboxylate moiety was reported to be an important pharmacophore of plant activators. In this study, a series of novel plant activators based on thieno[2,3-d]-1,2,3-thiadiazole-6-carboxylate were designed and synthesized and their biological activity as plant activators was studied. The structures of the novel compounds were identified by H-1 NMR, F-19 NMR and HRMS. The in vivo bioassay showed that these novel compounds had good efficacy against seven plant diseases. Especially, compounds 1a and 1c were more potent than the commercialized plant activator BTH. Almost no fungicidal activity was observed for the active compounds in the in vitro assay, which matched the requirements as plant activators. (C) 2013 Bao-Ju Li and Yu-Fang Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• A new type of plant activator: thieno[2,3-<i>d</i>][1,2,3]thiadiazole-6-carboxylic acid derivatives
  作者：Peter Stanetty、Manfred Kremslehner、Marion Jaksits

  DOI：10.1002/(sici)1096-9063(1998110)54:3<316::aid-ps838>3.0.co;2-c

  日期：1998.11

  A short and efficient synthesis of a series of the title compounds is presented starting with methylenebutanedioic acid and thioacetic acid. Using the: Hurd-Mori reaction in the key step, the optimised reaction sequence allows the large-scale preparation of this new type of plant activator in a few steps with a high overall yield. Additional functionalisation of the 5-position via directed ortho-lithiation methodology is also described. (C) 1998 Society of Chemical Industry.