3-amono-N-cyclopropyl-4-(thiophen-3-yl)benzenesulfonamide | 1604060-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amono-N-cyclopropyl-4-(thiophen-3-yl)benzenesulfonamide
• 英文别名: N-cyclopropyl-3-amino-4-(thiophen-3-yl)benzenesulfonamide；3-amino-N-cyclopropyl-4-(3-thienyl)benzenesulfonamide；3-amino-N-cyclopropyl-4-thiophen-3-ylbenzenesulfonamide
• CAS: 1604060-07-2
• 化学式: C₁₃H₁₄N₂O₂S₂
• 分子量: 294.398
• InChiKey: LLAPETXTFDWZMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amono-N-cyclopropyl-4-(thiophen-3-yl)benzenesulfonamide 以 乙腈 为溶剂， 生成 3-((5-chloro-6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)amino)-N-cyclopropyl-4-(thiophen-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Design and synthesis of novel 2-arylbenzimidazoles as selective mutant isocitrate dehydrogenase 2 R140Q inhibitors

  摘要：

  A series of novel 2-arylbenzimidazoles have been designed, synthesized and evaluated for their inhibitory activity against IDH2 R140Q mutant. The preliminary results indicated that four compounds 7b, 7c, 7m and 7r displayed the potent inhibitory activity against IDH2 R140Q mutant. Among them, compound 7c showed the highest inhibitory activity, with the IC50 value of 0.26 mu M, which was more active than positive control enasidenib. The exquisite selectivity of 7c for IDH2 R140Q mutant isoform was demonstrated by the poor activity against the IDH1 R132C mutant, IDH1 R132H mutant, wild-type IDH1, IDH2 R172K mutant and the wild-type IDH2.

  DOI：

  10.1016/j.bmcl.2020.127070
• 作为产物：
  描述：

  4-bromo-3-nitrobenzenesulfonyl chloride 在 吡啶 、 四(三苯基膦)钯 、 potassium acetate 、 氯化铵 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 3-amono-N-cyclopropyl-4-(thiophen-3-yl)benzenesulfonamide
  参考文献：
  名称：

  苯磺酰胺类IDH突变体抑制剂、其制备方法和用途

  摘要：

  本发明公开了一种通式(I)所示的苯磺酰胺类化合物或其药学上可接受的盐，及其制备方法和用途。相对于现有技术，本发明公开的苯磺酰胺类化合物能够作为异柠檬酸脱氢酶2(IDH2)突变体抑制剂。药理实验结果表明，本发明的化合物对IDH2突变体(mIDH2)活性具有明显的抑制作用，能够有效抑制mIDH2催化α‑酮戊二酸生成2‑羟基戊二酸的过程，可以用于预防和/或治疗IDH2突变所引起的各种相关疾病，包括癌症等。

  公开号：

  CN111662275B

文献信息

• 苯磺酰胺类IDH突变体抑制剂、其制备方法和用途
  申请人：中国药科大学

  公开号：CN111662275B

  公开（公告）日：2023-08-22

  本发明公开了一种通式(I)所示的苯磺酰胺类化合物或其药学上可接受的盐，及其制备方法和用途。相对于现有技术，本发明公开的苯磺酰胺类化合物能够作为异柠檬酸脱氢酶2(IDH2)突变体抑制剂。药理实验结果表明，本发明的化合物对IDH2突变体(mIDH2)活性具有明显的抑制作用，能够有效抑制mIDH2催化α‑酮戊二酸生成2‑羟基戊二酸的过程，可以用于预防和/或治疗IDH2突变所引起的各种相关疾病，包括癌症等。
• [EN] THERAPEUTIC COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ET COMPOSITIONS THÉRAPEUTIQUES
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2014062511A1

  公开（公告）日：2014-04-24

  Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).

  提供的是芳基磺酰胺二芳基脲衍生物化合物，它们是突变异柠檬酸脱氢酶1/2（IDH 1/2）的抑制剂，可用于治疗癌症。还提供了治疗癌症的方法，包括向需要的受试者施用本文描述的化合物。本发明的化合物可用于治疗的癌症包括胶质母细胞瘤、骨髓增生异常综合征、骨髓增生性肿瘤、急性髓系白血病、肉瘤、黑色素瘤、非小细胞肺癌、软骨肉瘤和非霍奇金淋巴瘤（NHL）。
• THERAPEUTIC COMPOUNDS AND COMPOSITIONS
  申请人：AGIOS PHARMACEUTICALS, INC.

  公开号：US20150299115A1

  公开（公告）日：2015-10-22

  Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).

  提供的是芳基磺酰胺二芳基脲衍生物化合物，它们是突变异柠檬酸脱氢酶1/2（IDH1/2）的抑制剂，用于治疗癌症。还提供了一种治疗癌症的方法，包括向需要治疗的受试者投与本文所述的化合物。本发明的化合物可治疗的癌症包括胶质母细胞瘤、骨髓增生异常综合征、骨髓增生性肿瘤、急性髓系白血病、肉瘤、黑色素瘤、非小细胞肺癌、软骨肉瘤和非霍奇金淋巴瘤（NHL）。
• Therapeutic compounds and compositions
  申请人：AGIOS PHARMACEUTICALS, INC.

  公开号：US10202339B2

  公开（公告）日：2019-02-12

  Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).

  本发明提供的芳基磺酰胺二芳基脲衍生物化合物是突变型异柠檬酸脱氢酶 1/2（IDH 1/2）的抑制剂，可用于治疗癌症。还提供了治疗癌症的方法，包括向有需要的受试者施用本文所述的化合物。本发明化合物可治疗的癌症包括胶质母细胞瘤、骨髓增生异常综合征、骨髓增生性肿瘤、急性骨髓性白血病、肉瘤、黑色素瘤、非小细胞肺癌、软骨肉瘤和非霍奇金淋巴瘤（NHL）。
• Design and synthesis of novel 2-arylbenzimidazoles as selective mutant isocitrate dehydrogenase 2 R140Q inhibitors
  作者：Zhenyu Li、Xingkang Wu、Lejiao Jia、Jun Li、Rui Zhang、Hui Tang、Zhiying Li、Huagang Bu、Chengwu Shen

  DOI：10.1016/j.bmcl.2020.127070

  日期：2020.5

  A series of novel 2-arylbenzimidazoles have been designed, synthesized and evaluated for their inhibitory activity against IDH2 R140Q mutant. The preliminary results indicated that four compounds 7b, 7c, 7m and 7r displayed the potent inhibitory activity against IDH2 R140Q mutant. Among them, compound 7c showed the highest inhibitory activity, with the IC50 value of 0.26 mu M, which was more active than positive control enasidenib. The exquisite selectivity of 7c for IDH2 R140Q mutant isoform was demonstrated by the poor activity against the IDH1 R132C mutant, IDH1 R132H mutant, wild-type IDH1, IDH2 R172K mutant and the wild-type IDH2.