1-[(5-bromo-2-oxoindol-3-yl)amino]-3-(4-bromophenyl)thiourea | 92461-02-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-(4-bromophenyl)thiourea
• CAS: 92461-02-4
• 化学式: C₁₅H₁₀Br₂N₄OS
• 分子量: 454.145
• InChiKey: PLLMKXDOJLGMIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-溴丙酸乙酯 、 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-(4-bromophenyl)thiourea 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到5-Bromo-3-{[3-(4-bromo-phenyl)-5-methyl-4-oxo-thiazolidin-(2E)-ylidene]-hydrazono}-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Synthesis and Primary Cytotoxicity Evaluation of New 5-Bromo-3-substituted-hydrazono-1H-2-indolinones

  摘要：

  In this study a new series of 5-bromo-3-[(3-subtituted-5-methyl-4-thiazolidinone-2-lidene)-hydrazono]-1H-2-indolinones (3a-i) and 5-bromo-3-[(2-thioxo-3-substituted-4,5-imidazolidinedione-1-yl)imino]-1H-2-indolinones (4a-f) was synthesized by the cyclization of 5-bromo-3-(N-substituted-thiosemicarbazono)-1 H-2-indolinones (2 a-i) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl cloride in anhydrous diethyl ether, respectively Six compounds chosen as prototypes were evaluated in the 3-cell line, one dose in vitro primary cytotoxicity assay. Four of them were evaluated against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. Among the compounds tested, the 4-fluorophenylthiosemicarbazone derivative 2f showed the most favorable cytotoxicity This compound demonstrated the most marked effects on a breast cancer cell line (BT-549, log(10)GI(50) value -6.40), a non small cell lung cancer cell line (NCl-H23, log(10)GI(50) value -6.10), and an ovarian cancer cell line (IGROV1, log(10)GI(50) value -6.02).

  DOI：

  10.1002/1521-4184(200211)335:8<374::aid-ardp374>3.0.co;2-k
• 作为产物：
  描述：

  5-溴靛红 、 4-(4-溴苯基)-3-氨基硫脲 以 乙醇 为溶剂， 反应 2.0h， 生成 1-[(5-bromo-2-oxoindol-3-yl)amino]-3-(4-bromophenyl)thiourea
  参考文献：
  名称：

  Synthesis and Primary Cytotoxicity Evaluation of New 5-Bromo-3-substituted-hydrazono-1H-2-indolinones

  摘要：

  In this study a new series of 5-bromo-3-[(3-subtituted-5-methyl-4-thiazolidinone-2-lidene)-hydrazono]-1H-2-indolinones (3a-i) and 5-bromo-3-[(2-thioxo-3-substituted-4,5-imidazolidinedione-1-yl)imino]-1H-2-indolinones (4a-f) was synthesized by the cyclization of 5-bromo-3-(N-substituted-thiosemicarbazono)-1 H-2-indolinones (2 a-i) with ethyl 2-bromopropionate in anhydrous ethanolic medium and oxalyl cloride in anhydrous diethyl ether, respectively Six compounds chosen as prototypes were evaluated in the 3-cell line, one dose in vitro primary cytotoxicity assay. Four of them were evaluated against the full panel of 60 human tumor cell lines at a minimum of five concentrations at 10-fold dilutions. Among the compounds tested, the 4-fluorophenylthiosemicarbazone derivative 2f showed the most favorable cytotoxicity This compound demonstrated the most marked effects on a breast cancer cell line (BT-549, log(10)GI(50) value -6.40), a non small cell lung cancer cell line (NCl-H23, log(10)GI(50) value -6.10), and an ovarian cancer cell line (IGROV1, log(10)GI(50) value -6.02).

  DOI：

  10.1002/1521-4184(200211)335:8<374::aid-ardp374>3.0.co;2-k

文献信息

• Syntheses of Some Substituted Isatin-β-thiosemicarbazones and Isatin-β-hydrazonothiazoline Derivatives as Potential Antiviral and Antimicrobial Agents
  作者：A.-Mohsen M. E. Omar、Nabil H. Eshba、Hassan M. Salama

  DOI：10.1002/ardp.19843170810

  日期：——

  A series of isatin‐β‐thiosemicarbazones and isatin‐β‐hydrazonothiazolines was synthesized by condensation of various isatin derivatives with N4‐substituted 3‐thiosemicarbazides and cyclization of the products by phenacyl bromides. The products showed high toxicity at lower concentrations when tested for antiviral activity against MDCK cells and did not exhibit antimicrobial activity against various

  通过各种靛红衍生物与N4取代的3-氨基硫脲缩合，再用苯甲酰溴环化产物，合成了一系列靛红-β-氨基硫脲和靛红-β-肼基噻唑啉。当测试对 MDCK 细胞的抗病毒活性时，该产品在较低浓度下表现出高毒性，并且对各种微生物没有表现出抗菌活性。
• [EN] THIOSEMICARBAZONES WITH MDR1 - INVERSE ACTIVITY<br/>[FR] THIOSEMICARBAZONES À ACTIVITÉ ANTI-MDR1
  申请人：US HEALTH

  公开号：WO2012033601A1

  公开（公告）日：2012-03-15

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure;Formula (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.

  本文披露了具有MDR逆转活性的药物化合物，因此对多药耐药细胞有效。本文披露的示例化合物具有下列结构；公式（I）。已发现披露的化合物的示例具有直接治疗多药耐药细胞的功效，使多药耐药细胞对其他化疗药物敏感，并在某些情况下逆转多药耐药。
• Karali; Gursoy, Il Farmaco, 1994, vol. 49, # 12, p. 819 - 822
  作者：Karali、Gursoy

  DOI：——

  日期：——
• AQUA MEDIATED ONE POT FACILE SYNTHESIS OF NOVEL THIOXO-1,2,4-TRIAZIN-5(2H)-ONE AND [1,2,4] TRIAZINO[5,6-A]INDOLE DERIVATIVES AND THEIR BIOLOGICAL ACTIVITIES
  作者：HARSHITA SACHDEVA、DIKSHA DWIVEDI、HAR LAL SINGH、KANTI PRAKASH SHARM

  DOI：10.4067/s0717-97072012000400004

  日期：——

  Rapid and highly efficient one pot green chemical synthesis of substituted 6-(2-aminophenyl)-4-(4-substitutedphenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one and 8-substituted-3,5-dihydro-2H-[1,2,4]triazino[5,6-b]indole is carried out in aqueous medium under microwave irradiation. Improved synthesis of potent bioactive Schiff and N-Mannich bases of hexahydro-1H-indole-2,3-dione is also reported. The title compounds are easily accessible by various approaches; even waste free approaches have been developed. The operational simplicity, environmentally benign conditions and high yield achieved in a very short reaction time are major benefits that meet the requirements of green production, including saving energy and high efficiency. The results obtained under microwaves are compared with that of conventional heating. Structural assignments are based on spectroscopic data. Compounds have also been screened for antibacterial and antifungal activities.
• OMAR, A. -M. M. E.;ESHBA, N. H.;SALAMA, H. M., ARCH. PHARM., 1984, 317, N 8, 701-709
  作者：OMAR, A. -M. M. E.、ESHBA, N. H.、SALAMA, H. M.

  DOI：——

  日期：——