4-(3-硫代脲啶)苯磺酰胺 | 1718-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3-硫代脲啶)苯磺酰胺
• 中文别名: 4-硫脲基-苯磺酰胺
• 英文名称: (4-aminosulfonylphenyl)thiourea
• 英文别名: 4-[(aminocarbothioyl)amino]benzenesulfonamide；4-(3-thioureido)benzene sulfonamide；N-(4-aminosulfonylphenyl)thiourea；4-thioureidobenzenesulfonamide；4-aminosulfonylphenylthiourea；4-thioureido-benzenesulfonamide；(4-sulfamoylphenyl)thiourea
• CAS: 1718-39-4
• 化学式: C₇H₉N₃O₂S₂
• mdl: MFCD00775046
• 分子量: 231.299
• InChiKey: OGAAVFJBPHTLNL-UHFFFAOYSA-N

物化性质

• 熔点：
  209 °C
• 沸点：
  448.0±55.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P270,P264,P301+P310+P330,P405
• 危险品运输编号：
  2811
• 危险性描述：
  H301
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4-(3-硫代脲啶)苯磺酰胺 在 sodium acetate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  New benzenesulfonamide scaffold-based cytotoxic agents: Design, synthesis, cell viability, apoptotic activity and radioactive tracing studies

  摘要：

  A new series of thiazolidinone (5a-g), thiazinone (9a-g) and dithiazepinone (9a-g) heterocycles bearing a benzenesulfonamide scaffold was synthesized. Cytotoxicity of these derivatives was assessed against MCF-7, HepG2, HCT-116 and A549 cancer cell lines and activity was compared to the known cytotoxic agents doxorubicin and 5-FU where the most active compounds displayed better to nearly similar IC50 values to the reference compounds. For assessing selectivity, the most active derivatives against MCF-7, 5b, 5c and 5e, were also assessed against the normal breast cell line MCF-10 A where they demonstrated high selective cytotoxicity to cancerous cells over that to normal cells. Further, the effect of the most active compounds 5b-e on MCF-7 and HepG2 cell cycle phase distribution was assessed and the tested sulfonamide derivatives were found to induce accumulation of cells in the < 2n phase. To further confirm apoptosis induction, caspase 8 and 9 levels in MCF-7 and HepG2 were evaluated before and after treatment with compounds 5b-e and were found to be significantly higher after exposure to the test agents. Since 5c was the most active, its effect on the cell cycle regulation was confirmed where it showed inhibition of the CDK2/cyclin E1. Finally, in vivo biodistribution study using radioiodinated-5c revealed a significant uptake and targeting ability into solid tumor in a xenograft mouse model.

  DOI：

  10.1016/j.bioorg.2020.103577
• 作为产物：
  描述：

  磺胺 在 potassium thioacyanate 作用下， 以99 %的产率得到4-(3-硫代脲啶)苯磺酰胺
  参考文献：
  名称：

  NOVEL INHIBITORS OF LYSYL OXIDASES

  摘要：

  Described herein are novel compounds that block the activity of LOX family members having good IC50 values, no cellular toxicity below 10 μM, induce sensitization of the cells to doxorubicin, strong activity in a recombinant LOX/LOXL2 activity, and a chemical structure that is drug-like and does not have a PAINS flag, as well as, methods of treatment using the compounds with respect to cancer, organ fibrosis, neurodegenerative and cardiovascular diseases.

  公开号：

  US20220378753A1

文献信息

• Synthesis and evaluation of sulfonamide-bearing thiazole as carbonic anhydrase isoforms hCA I and hCA II
  作者：Soner Kılıcaslan、Mustafa Arslan、Zeynep Ruya、Çigdem Bilen、Adem Ergün、Nahit Gençer、Oktay Arslan

  DOI：10.3109/14756366.2015.1128426

  日期：2016.11.1

  (Ki) were determined. The results showed that all the synthesized compounds inhibited the CA isoenzyme activity. Among them 5b was found to be the most active (IC50 = 0.35 μM; Ki: 0.33 μM) for hCA I and hCA II.

  合成了带有磺酰胺的噻唑化合物，并评估了它们对纯化的人碳酸酐酶I和II活性的抑制作用。通过亲和色谱法从红细胞中纯化人碳酸酐酶同工酶（hCA-I和hCA-II）。在体外研究了12种合成的磺酰胺（5A-1）对这些同功酶（hCA-1和hCA-2）的水合酶和酯酶活性的抑制作用。关于这些活性，确定了抑制平衡常数（Ki）。结果表明，所有合成的化合物均抑制了CA同工酶的活性。其中5b被发现对hCA I和hCA II最有活性（IC50 = 0.35μM; Ki：0.33μM）。
• [EN] INHIBITORS OF Akt ACTIVITY<br/>[FR] INHIBITEURS DE L'ACTIVITE DE AKT
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005011700A1

  公开（公告）日：2005-02-10

  Invented are novel 1 H-imidazo[4,5-c]pyridin-2-yI compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.

  发明了新型的1H-咪唑[4,5-c]吡啶-2-基化合物，这些化合物用作蛋白激酶B活性的抑制剂，并用于治疗癌症和关节炎。
• Thiourea carbonic anhydrase inhibitors and their use in treatment of glaucoma
  申请人：Casini, Angela

  公开号：EP1421935A1

  公开（公告）日：2004-05-26

  Carbonic anhydrase inhibitory compounds which incorporate a 4-sulfamoylphenylmethylthiourea scaffold are disclosed. The new compounds show strong affinities toward carbonic anhydrase isozymes I, II and IV and produce effective and prolonged reduction in intraocular pressure following topical ocular administration. The compounds are useful in treating glaucoma or ocular hypertension.

  抑制性碳酸酐酶化合物，其中包括4-磺胺基苯甲基硫脲骨架。这些新化合物对碳酸酐酶同工酶I、II和IV具有很强的亲和力，并在局部眼用给药后产生有效且持久的降低眼压作用。这些化合物可用于治疗青光眼或眼压增高。
• 一种5-(1H-吲哚-3-亚甲基)-1,3-噻唑烷-4- 酮类衍生物及其合成方法和应用
  申请人：西安交通大学

  公开号：CN104059060B

  公开（公告）日：2017-08-01

  一种5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用，以乙醇和或水为溶剂，将取代2‑取代亚氨基‑1,3‑噻唑烷‑4‑酮与1H‑吲哚‑3‑甲醛在哌啶催化条件下，回流反应，通过分子间脱水缩合反应形成亚甲基连接基，得到5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物。其中所涉及的中间体2‑取代亚氨基噻唑烷‑4‑酮是由各种单取代的硫脲氯乙酸乙酯或氯乙酸在低沸点溶剂中经回流条件下的环合反应制备而得，中间体2‑取代亚氨基‑3‑取代‑1,3,‑噻唑烷‑4‑酮由各种双取代的对称硫脲和氯乙酸通过绿色环保合成工艺制备。对所有目标化合物在酶分子水平上的生物活性初步筛选实验结果显示，目标产物对PTP1B和CDC25B在不同程度上显示一定的抑制活性。
• Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
  申请人：G. D. Searle & Co.

  公开号：US06388132B1

  公开（公告）日：2002-05-14

  Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

  选定的双氨基酸羟乙基氨基磺胺化合物作为逆转录病毒蛋白酶抑制剂具有良好的效果，特别是作为HIV蛋白酶的抑制剂。本发明涉及这类逆转录病毒蛋白酶抑制剂，更具体地涉及选定的新化合物、组合物和方法，用于抑制逆转录病毒蛋白酶，如人类免疫缺陷病毒（HIV）蛋白酶，预防逆转录病毒感染或传播，以及治疗逆转录病毒感染。