5-bromoisatin 3-thiosemicarbazone | 4553-11-1

• 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: 5-bromoisatin 3-thiosemicarbazone
• 英文别名: [(5-bromo-2-oxoindol-3-yl)amino]thiourea
• CAS: 4553-11-1
• 化学式: C₉H₇BrN₄OS
• mdl: MFCD00459307
• 分子量: 299.151
• InChiKey: BWOCZUHJZYNGIK-UHFFFAOYSA-N

物化性质

• 熔点：
  271-272 °C
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.51
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromoisatin 3-thiosemicarbazone 在 NaOH adsorbed on neutral alumina 作用下， 以 水 为溶剂， 生成 5-oxo-6-(2-amino-5-bromophenyl)-1,2,4-triazine-3-thione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.4067/s0717-97072012000400004
• 作为产物：
  描述：

  5-bromo-N-acetylisatinic acid thiosemicarbazide 在 盐酸 作用下， 反应 0.5h， 以90.4%的产率得到5-bromoisatin 3-thiosemicarbazone
  参考文献：
  名称：

  Tomchin, A. B., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 4, p. 737 - 747

  摘要：

  DOI：

文献信息

• Assessment of 5-substituted Isatin as Surface Recognition Group: Design, Synthesis, and Antiproliferative Evaluation of Hydroxamates as Novel Histone Deacetylase Inhibitors
  作者：Avineesh Singh、Kamlesh Raghuwanshi、Vijay K Patel、Deepak K Jain、Ravichandran Veerasamy、Anshuman Dixit、Harish Rajak

  DOI：10.1007/s11094-017-1616-1

  日期：2017.8

  Histone deacetylase (HDAC) is a promising target for cancer treatment. HDAC inhibitors consist of three pharmacophoric features: an aromatic cap group, zinc binding group (ZBG), and a linker chain connecting cap group to ZBG. Herein, we report on (i) substituted isatin moiety as the cap group that recognizes the surface of active enzyme pocket and (ii) thiosemicarbazide moiety incorporated as linker group responsible for connecting the cap group to ZBG (hydroxamic acid). The synthesized compounds were evaluated for their antiproliferative activity and HDAC enzyme inhibition. The binding mode analysis of proposed compounds was evaluated by docking studies. Several analogs were found to inhibit HDAC and cellular proliferation of Hela cervical cancer cells, with GI50 values in the micromolar range. One compound (Vd) was found to have greater in vitro antiproliferative activity in comparison to other compounds.

  组蛋白去乙酰化酶（HDAC）是癌症治疗的潜在靶点。HDAC抑制剂由三种药效团特征组成：芳香的帽状基团、锌结合基团（ZBG）以及连接帽状基团与ZBG的链接链。本文报道了（i）取代的异吲哚酮部分作为帽状基团，识别活性酶口袋表面，以及（ii）结合为链接基团负责连接帽状基团与ZBG（羟肟酸）的酰肼部分。所合成的化合物进行了抗增殖活性和HDAC酶抑制活性的评估。通过对接研究评估了所提出化合物的结合模式。发现多个类似物能够抑制HDAC及宫颈癌Hela细胞的增殖，其GI50值在微摩尔范围内。其中一个化合物（Vd）相较于其他化合物显示出更强的体外抗增殖活性。
• One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe ₃ O ₄ MNPs as highly effective nanocatalyst
  作者：Zohreh Esam、Malihe Akhavan、Ahmadreza Bekhradnia

  DOI：10.1002/aoc.6005

  日期：2021.1

  (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives via a one‐pot multiple‐component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic

  已经成功地报道了将磺酸固定在Fe 3 O 4磁性纳米颗粒（MNPs）表面上作为新型酸纳米催化剂。制备的超顺磁性核-壳（Fe 3 O 4 @ PFBA-Metformin @ SO 3的形态特征，热稳定性，磁性和其他物理化学性质H）使用傅里叶变换红外（FTIR），X射线衍射（XRD），能量色散X射线光谱（EDS），场发射扫描电子显微镜（FESEM），透射电子显微镜（TEM），热重分析–差示热分析（TGA-DTA），原子力显微镜（AFM），动态光散射（DLS），布鲁诺尔-埃米特-泰勒（BET）和振动样品磁力计（VSM）技术。它是在绿色条件下通过单锅多组分级联反应合成2-（哌嗪-1-基）喹喔啉和苯并咪唑衍生物的一种有效且可重复使用的催化剂。结果表明，Fe 3 O 4 @ PFBA–metformin @ SO 3具有优异的催化活性。H作为有机-无机杂化纳米催化剂，用于缩合和多组分曼尼希型反应。该
• Manganese(II) complexes of biological relevance: Synthesis and spectroscopic characterization of novel manganese(II) complexes with monobasic bidentate ligands derived from halo-substituted 1H-indole-2,3-diones
  作者：S. Sharma、R. Meena、Y. Satyawana、N. Fahmi

  DOI：10.1134/s1070363216120446

  日期：2016.12

  synthesized metal complexes. The ligands and complexes were tested in vitro against bacteria (Escherichia coli and Staphylococcus aureus) and fungi (Fusarium semitectum and Aspergillus flavus) to show that they were active against all the microbial strains examined, and the metal complexes were more active in comparison with the ligands. DNA cleavage activity of the complexes was examined by gel electrophoresis

  具有四个一元二齿配体L 1 H [2-（5-氟-2-二氢-2-氧-2-氧-1 H-吲哚-3-亚烷基）肼甲酰胺]，L 2 H [2- （5-氟-2-二氢-2-氧-1 H-吲哚-3-亚烷基）肼甲硫代酰胺]，L 3 H [2-（5-溴-2-二氢-2-氧-2-氧-1 H-吲哚-3 -配体与MnCl 2 ·4H 2配位合成了L- 4 H [2-亚甲基]肼甲酰胺]和L 4 H [2-（5-溴-2-二氢-2-氧代-1 H-吲哚-3-亚甲基）肼甲硫酰胺]在甲醇中摩尔比为1：1和1：2。Schiff碱配体和络合物的特征在于元素分析，熔点，分子量，IR，1 H和13 C NMR，UV-Vis，EPR和质谱以及X射线粉末衍射图。根据光谱数据，提出了所有合成金属配合物的四面体几何形状。在体外测试了配体和复合物对细菌（大肠杆菌和金黄色葡萄球菌）和真菌（半镰刀菌和黄曲霉）的抵抗力。）表明它们对所有检测的微生物菌株均具
• Solvent-free microwave-assisted synthesis of 1<i>H</i>-indole-2, 3-dione derivatives
  作者：Ashish Kumar Singh、Sudhish Kumar Shukla、Ishtiaque Ahamad、M. A. Quraishi

  DOI：10.1002/jhet.131

  日期：2009.5

  Microwave-assisted synthesis has been found to increase both reaction rates and yields via more efficient heating compared with standard thermal conduction. Dry reaction of isatins with thiosemicarbazide and their thiosemicarbazone with secondary amine on acid—washed K10 in microwave oven afforded isatin-3-thiosemicarbazones and N-Mannich bases in reasonably good yield. The chemical structures were

  已经发现，与标准的热传导相比，微波辅助合成通过更有效的加热可以提高反应速率和产率。Isatin与thiosemicarbazide以及它们的thiosemicarbazone与仲胺在酸上的干反应-在微波炉中洗涤K10，可以得到相当好的产率的isatin-3-thiosemicarbazones和N-Mannich碱。化学结构通过1 H NMR，IR光谱数据和元素分析得到确认。J.杂环化​​学。，46，571（2009）。
• Microwave-Assisted Synthesis of Some Novel Thiazolidinone and Thiohydantoin Derivatives of Isatins
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1080/10426500903567554

  日期：2010.10.28

  A simple, rapid, and efficient method for the synthesis of some new thiazolidinone and thiohydantoin derivatives of isatins along with some Mannich bases has been achieved in excellent yield from indole-2,3-dione-3-thiosemicarbazone employing microwave irradiation.

  一种简单、快速和有效的方法，用于合成一些新的靛红噻唑烷酮和硫代乙内酰脲衍生物以及一些曼尼希碱，使用微波辐射从 indole-2,3-dione-3-thiosemicarbazone 中获得了极好的收率。