1-(2-chlorophenyl)-3-(4-amino-5-thioxo-1,2,4-triazol-3-yl) β-carboline | 1085709-01-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(2-chlorophenyl)-3-(4-amino-5-thioxo-1,2,4-triazol-3-yl) β-carboline
• 英文别名: 4-amino-3-[1-(2-chlorophenyl)-9H-pyrido[3,4-b]indol-3-yl]-1H-1,2,4-triazole-5-thione
• CAS: 1085709-01-8
• 化学式: C₁₉H₁₃ClN₆S
• 分子量: 392.871
• InChiKey: BVMQJSHXRWTFHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-chlorophenyl)-3-(4-amino-5-thioxo-1,2,4-triazol-3-yl) β-carboline 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 12.0h， 以70%的产率得到
  参考文献：
  名称：

  新型的1-取代的3-（4,5-取代的1,2,4-三唑-3-基）-β-咔啉衍生物的合成及抗肿瘤活性

  摘要：

  摘要 席夫碱，1,2,4-三唑[4,3- d ] [1,2,3,4]噻三唑和1,2,4-三唑[3,4- b ] [1,3,4]由3-（4-氨基-5-巯基-1,2,4-三唑-3-基）-β-咔啉合成带有β-咔啉核的噻二唑。评价化合物对八种人类癌细胞系的体外抗肿瘤活性。1,2,4-三唑并[4,3- d ] [1,2,3,4]噻三唑衍生物显示出广谱的抗肿瘤活性，所有测试的细胞系的GI 50值均低于13μM。通常，所有测试的化合物均显示出对乳腺癌（MCF-7）癌细胞系的有效活性，GI 50值在2.07至4.58μM的范围内。 席夫碱，1,2,4-三唑[4,3- d ] [1,2,3,4]噻三唑和1,2,4-三唑[3,4- b ] [1,3,4]由3-（4-氨基-5-巯基-1,2,4-三唑-3-基）-β-咔啉合成带有β-咔啉核的噻二唑。评价化合物对八种人类癌细胞系的体外抗肿瘤活性。1,2,4-三唑并[4

  DOI：

  10.1055/s-0037-1610291
• 作为产物：
  描述：

  1-(o-chlorophenyl)-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline 在 肼 作用下， 反应 96.0h， 生成 1-(2-chlorophenyl)-3-(4-amino-5-thioxo-1,2,4-triazol-3-yl) β-carboline
  参考文献：
  名称：

  Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives

  摘要：

  Several novel 1-substituted-phenyl beta-carbolines bearing the 2-substituted-1,3,4-oxadiazol-5-yl and 5-substituted-1,2,4-triazol-3-yl groups at C-3 were synthesized and evaluated for their in vitro anticancer activity. The assay results pointed thirteen compounds with growth inhibition effect (GI(50) < 100 mu M) for all eight different types of human cancer cell lines tested. The b-carbolines 7a and 7h, bearing the 3-(2-metylthio-1,3,4-oxadiazol-5-yl) group, displayed high selectivity and potent anticancer activity against ovarian cell line with GI50 values lying in the nanomolar concentration range (GI(50) = 10 nM for both compounds). The 1-(N,N-dimethylaminophenyl)-3-(5-thioxo-1,2,4-triazol-3-yl) beta-carboline (8g) was the most active compound, showing particular effectiveness on lung (GI(50) = 0.06 mu M), ovarian and renal cell lines. The potent anticancer activity presented for synthesized compounds 7a, 7h, and 8g, together with their easiness of synthesis, makes these compounds promising anticancer agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.008

文献信息

• Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl) β-carboline derivatives
  作者：Anelise S. Nazari Formagio、Lilian T. Düsman Tonin、Mary Ann Foglio、Christiana Madjarof、João Ernesto de Carvalho、Willian Ferreira da Costa、Flávia P. Cardoso、Maria Helena Sarragiotto

  DOI：10.1016/j.bmc.2008.10.008

  日期：2008.11

  Several novel 1-substituted-phenyl beta-carbolines bearing the 2-substituted-1,3,4-oxadiazol-5-yl and 5-substituted-1,2,4-triazol-3-yl groups at C-3 were synthesized and evaluated for their in vitro anticancer activity. The assay results pointed thirteen compounds with growth inhibition effect (GI(50) < 100 mu M) for all eight different types of human cancer cell lines tested. The b-carbolines 7a and 7h, bearing the 3-(2-metylthio-1,3,4-oxadiazol-5-yl) group, displayed high selectivity and potent anticancer activity against ovarian cell line with GI50 values lying in the nanomolar concentration range (GI(50) = 10 nM for both compounds). The 1-(N,N-dimethylaminophenyl)-3-(5-thioxo-1,2,4-triazol-3-yl) beta-carboline (8g) was the most active compound, showing particular effectiveness on lung (GI(50) = 0.06 mu M), ovarian and renal cell lines. The potent anticancer activity presented for synthesized compounds 7a, 7h, and 8g, together with their easiness of synthesis, makes these compounds promising anticancer agents. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives
  作者：Maria Sarragiotto、George Brand、Carla Gomes、Willian Costa、Mary Foglio、Ana Ruiz

  DOI：10.1055/s-0037-1610291

  日期：2019.1

  Abstract Schiff bases, 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles, and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles carrying the β-carboline nucleus were synthesized from 3-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-β-carbolines. The compounds were evaluated for their in vitro antitumor activity against eight human cancer cell lines. The 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazole derivatives showed a broad

  摘要 席夫碱，1,2,4-三唑[4,3- d ] [1,2,3,4]噻三唑和1,2,4-三唑[3,4- b ] [1,3,4]由3-（4-氨基-5-巯基-1,2,4-三唑-3-基）-β-咔啉合成带有β-咔啉核的噻二唑。评价化合物对八种人类癌细胞系的体外抗肿瘤活性。1,2,4-三唑并[4,3- d ] [1,2,3,4]噻三唑衍生物显示出广谱的抗肿瘤活性，所有测试的细胞系的GI 50值均低于13μM。通常，所有测试的化合物均显示出对乳腺癌（MCF-7）癌细胞系的有效活性，GI 50值在2.07至4.58μM的范围内。 席夫碱，1,2,4-三唑[4,3- d ] [1,2,3,4]噻三唑和1,2,4-三唑[3,4- b ] [1,3,4]由3-（4-氨基-5-巯基-1,2,4-三唑-3-基）-β-咔啉合成带有β-咔啉核的噻二唑。评价化合物对八种人类癌细胞系的体外抗肿瘤活性。1,2,4-三唑并[4