5-chloroisatin 3-thiosemicarbazone | 4501-83-1

• 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-chloroisatin 3-thiosemicarbazone
• 英文别名: [(5-chloro-2-oxoindol-3-yl)amino]thiourea
• CAS: 4501-83-1
• 化学式: C₉H₇ClN₄OS
• 分子量: 254.7
• InChiKey: WYKMFJVTKXILQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 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：
  2.0

反应信息

• 作为反应物：
  描述：

  5-chloroisatin 3-thiosemicarbazone 在 NaOH adsorbed on neutral alumina 作用下， 以 水 为溶剂， 生成 6-(2-Amino-5-chlorophenyl)-3,4-dihydro-3-thioxo-1,2,4-triazin-5(2H)-one
  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：

  4-氯苯胺盐酸盐 在 硫酸 、 盐酸羟胺 、 sodium sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.17h， 生成 5-chloroisatin 3-thiosemicarbazone
  参考文献：
  名称：

  Gupta, Neeti; Singh, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1998, vol. 37, # 1, p. 75 - 79

  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。
• Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors
  作者：Zhenzhen Xie、Guangcheng Wang、Jing Wang、Ming Chen、Yaping Peng、Luyao Li、Bing Deng、Shan Chen、Wenbiao Li

  DOI：10.3390/molecules22040659

  日期：——

  4-position of the right phenyl and 2-fluorobenzyl substituent at the N1-positions of the 5-methylisatin displayed the highest inhibitory activity with an IC50 value of 5.36 ± 0.13 μm. Molecular docking studies revealed the existence of hydrophobic interaction, CH-π interaction, arene-anion interaction, arene-cation interaction, and hydrogen bond between these compounds and α-glucosidase enzyme.

  合成了一系列新的靛红-噻唑衍生物并筛选了它们的体外 α-葡萄糖苷酶抑制活性。与标准药物阿卡波糖 (IC50 = 817.38 ± 6.27 μm) 相比，这些化合物显示出不同程度的 α-葡萄糖苷酶抑制活性，IC50 范围为 5.36 ± 0.13 至 35.76 ± 0.31 μm。在该系列中，化合物6p在右苯基的4-位带有羟基，在5-甲基靛红的N1-位带有2-氟苄基取代基，显示出最高的抑制活性，IC50值为5.36±0.13 μm。分子对接研究揭示了这些化合物与α-葡萄糖苷酶之间存在疏水相互作用、CH-π相互作用、芳烃-阴离子相互作用、芳烃-阳离子相互作用以及氢键。
• Synthesis and antibacterial activity of Schiff bases of 5-substituted isatins
  作者：Kamaleddin Haj Mohammad Ebrahim Tehrani、Maryam Hashemi、Maryam Hassan、Farzad Kobarfard、Shohreh Mohebbi

  DOI：10.1016/j.cclet.2015.10.027

  日期：2016.2

  Abstract Based on the existing reports on the bioactive isatin derivatives, a number of Schiff bases were synthesized by reacting 5-substituted isatins with bioactive amines/hydrazides and their structures were confirmed using spectroscopic methods such as NMR, IR and mass spectrometry. Furthermore, N -benzylation of isatin followed by the Schiff base formation furnished a new series of compounds (

  摘要根据已有的有关生物活性靛红衍生物的报道，通过5-取代的靛红与生物活性胺/酰肼的反应合成了许多席夫碱，并通过核磁共振，红外光谱和质谱等方法证实了其结构。此外，通过对Isatin进行N-苄基化和随后形成Schiff碱，提供了一系列新化合物（11a-13c），该化合物可以分析Isatin N-取代对所得化合物生物活性的影响。使用微量滴定板法对一系列革兰氏阳性和革兰氏阴性细菌菌株评估了合成衍生物的抗菌活性。化合物2d，3b，5c和6a是针对铜绿假单胞菌的最有效衍生物（MIC = 6.25μg/ mL）。对结构-活性关系的分析表明，掺入基于（硫）脲的席夫碱可产生更有效的衍生物，并具有更广泛的抗菌活性。此外，高度亲脂性化合物（如11a-12c）未显示任何可测量的抗菌活性，这意味着最佳的亲脂性可能是所研究的isatins抗菌活性的重要要求。最后，发现N-苄基异丁香酮的乙内酰脲衍生物（13a-13c）
• 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
• Microwave Irradiation for Accelerating each Step for the Synthesis of 1,2,4-Triazino[5,6-<i>b</i>]indole-3-thiolsand their Derivatives from Isatin and 5-Chloroisatin
  作者：El Sayed H. El Ashry、El Sayed Ramadan、Hamida M. Hamid、Mohamed Hagar

  DOI：10.1055/s-2004-815437

  日期：——

  Microwave irradiation has been used to accelerate the conversion of isatin (1), 5-chloroisatin (2), and N-benzylisatin (3) to their thiosemicarbazones and their subsequent cyclization into 1,2,4-triazino[5,6-b]indole-3-thiols 7 and 8; and the N-benzyl derivative 9. Selective and complete alkylation of 1, 7, 8, and 9 has also been achieved under microwave irradiation.

  微波辐射已被用于加速异靛（1）、5-氯异靛（2）和N-苄基异靛（3）转化为其硫脲衍生物，并随后环化为1,2,4-三氮唑[5,6-b]吲哚-3-硫醇7和8，以及N-苄基衍生物9。在微波辐射下，1、7、8和9的选择性和完全烷基化也已实现。