2-(3-(5-amino-1,3,4-thiadiazol-2-yl)propyl)isoindoline-1,3-dione | 182125-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(3-(5-amino-1,3,4-thiadiazol-2-yl)propyl)isoindoline-1,3-dione
• 英文别名: 2-[3-(5-amino-1,3,4-thiadiazol-2-yl)propyl]-1H-isoindole-1,3(2H)-dione；2-[3-(5-amino-1,3,4-thiadiazol-2-yl)propyl]isoindole-1,3-dione
• CAS: 182125-25-3
• 化学式: C₁₃H₁₂N₄O₂S
• 分子量: 288.33
• InChiKey: WHJDTNIXSFPLFF-UHFFFAOYSA-N

物化性质

• 沸点：
  515.953±52.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.474±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-(5-amino-1,3,4-thiadiazol-2-yl)propyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3-[5-(2,4,6-Triphenylpyridin-1-ium-1-yl)-1,3,4-thiadiazol-2-yl]propan-1-amine;perchlorate
  参考文献：
  名称：

  Carbonic anhydrase activators. Part 14. Syntheses of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II

  摘要：

  Reaction of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole with 2,4,6-trisubstituted pyrylium salts in molar ratios of 1:1 and 1:2 afforded three series of derivatives which were investigated for their abilities to activate the enzyme carbonic anhydrase (CA). Only compounds possessing free aminoalkyl moieties behaved as strong CA II activators, presumably via a mechanism involving the shuttling of protons between the enzyme active site and the environment.

  DOI：

  10.1016/0223-5234(96)89555-9
• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁酰氯 在 吡啶 、 硫酸 作用下， 反应 3.25h， 生成 2-(3-(5-amino-1,3,4-thiadiazol-2-yl)propyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Carbonic anhydrase activators. Part 14. Syntheses of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II

  摘要：

  Reaction of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole with 2,4,6-trisubstituted pyrylium salts in molar ratios of 1:1 and 1:2 afforded three series of derivatives which were investigated for their abilities to activate the enzyme carbonic anhydrase (CA). Only compounds possessing free aminoalkyl moieties behaved as strong CA II activators, presumably via a mechanism involving the shuttling of protons between the enzyme active site and the environment.

  DOI：

  10.1016/0223-5234(96)89555-9

文献信息

• Discovery of novel hydroxyamidine based indoleamine 2,3-dioxygenase 1 (IDO1) and thioredoxin reductase 1 (TrxR1) dual inhibitors
  作者：Ji Zhou、Li-Zhen Yu、Ya-Li Fan、Ci-Hao Guo、Xiao-Mei Lv、Zhi-Yin Zhou、Hui-Dan Huang、Dong-Dong Miao、Sheng-Peng Zhang、Xin-Yu Li、Ping-Ping Zhao、Xiao-Ping Liu、Wei-Hua Hu、Chao Zhang

  DOI：10.1016/j.ejmech.2022.114860

  日期：2023.1

  antitumor agents, novel dual indoleamine 2,3- dioxygenase 1 (IDO1) and thioredoxin reductase 1 (TrxR1) inhibitors were designed. Thioredoxin reductase 1 (TrxR1) is a main ROS modulator within CRC cells. Indoleamine 2,3-dioxygenase (IDO1) is crucial controller for tryptophan (Trp) metabolism that is also important for CRC immunotherapy. Herein, ten compounds 12a-j containing hydroxyamidine scaffold were designed

  为了利用免疫治疗和代谢抗肿瘤药物的优势，设计了新型双重吲哚胺 2,3-双加氧酶 1 (IDO1) 和硫氧还蛋白还原酶 1 (TrxR1) 抑制剂。硫氧还蛋白还原酶 1 (TrxR1) 是 CRC 细胞内的主要 ROS 调节剂。吲哚胺 2,3-双加氧酶 (IDO1) 是色氨酸 (Trp) 代谢的关键控制器，对于 CRC 免疫治疗也很重要。在此，设计、合成了十种含有羟基脒支架的化合物12a-j ，并评估了其对 IDO1/TrxR1 酶和 CRC 细胞的抑制活性。在这些化合物中，活性最强的化合物12d (ZC0109)对 IDO1 (IC 50  = 0.05 μM) 和 TrxR1 (IC 50 = 3.00 ± 0.25 μM) 被选择用于进一步评估。化合物ZC0109在体外和体内均对IDO1和TrxR1表现出良好的双重抑制作用。进一步的机制研究表明，通过ZC0109处理抑制 IDO1 和 TrxR1，累积的
• Abolishing Dopamine D_2long/D₃ Receptor Affinity of Subtype-Selective Carbamoylguanidine-Type Histamine H₂ Receptor Agonists
  作者：Katharina Tropmann、Merlin Bresinsky、Lisa Forster、Denise Mönnich、Armin Buschauer、Hans-Joachim Wittmann、Harald Hübner、Peter Gmeiner、Steffen Pockes、Andrea Strasser

  DOI：10.1021/acs.jmedchem.1c00692

  日期：2021.6.24
• Carbonic anhydrase activators. Part 14. Syntheses of mono and bis pyridinium salt derivatives of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole and their interaction with isozyme II
  作者：CT Supuran、M Barboiu、C Luca、E Pop、ME Brewster、A Dinculescu

  DOI：10.1016/0223-5234(96)89555-9

  日期：1996.1

  Reaction of 2-amino-5-(2-aminoethyl)- and 2-amino-5-(3-aminopropyl)-1,3,4-thiadiazole with 2,4,6-trisubstituted pyrylium salts in molar ratios of 1:1 and 1:2 afforded three series of derivatives which were investigated for their abilities to activate the enzyme carbonic anhydrase (CA). Only compounds possessing free aminoalkyl moieties behaved as strong CA II activators, presumably via a mechanism involving the shuttling of protons between the enzyme active site and the environment.