1-(6-bromohexyl)indoline-2,3-dione | 1138761-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(6-bromohexyl)indoline-2,3-dione
• 英文别名: 1-(6-Bromohexyl)indole-2,3-dione
• CAS: 1138761-72-4
• 化学式: C₁₄H₁₆BrNO₂
• 分子量: 310.191
• InChiKey: NLPHFKCUDGGSRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-bromohexyl)indoline-2,3-dione 以 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 1-(6-bromohexyl)-3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)spiro[indoline-3,2-thiazolidine]-2,4-dione
  参考文献：
  名称：

  Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents

  摘要：

  A series of novel spiro[indole-thiazolidine]spiro[indole-pyran] derivatives were synthesized from N-(bromoalkyl)indol-2,3-diones via monospiro-bisindole intermediates; the two indole nuclei being connected via N-(CH2)(n)-N linker. Synthesized compounds were evaluated for their antimicrobial activities in vitro against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Staphylococcus epidermis), four Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, and Klebsiella pneumonia) as well as four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, and Candida albicans) using Cup plate method. Bis spiro-indoles exhibited stronger antibacterial and antifungal efficiency than their corresponding mono spiro-indoles. Compound 10e, the most active derivative was shown to inhibit the growth of all bacterial strains and two fungal strains (A. niger and C. albicans) (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.121
• 作为产物：
  描述：

  1,6-二溴己烷 、 靛红 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(6-bromohexyl)indoline-2,3-dione
  参考文献：
  名称：

  Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids

  摘要：

  一种简单直接的合成方法，用于潜在的抗感染硫代内酯-异喹啉杂合物的研究，发现了一种新型四环化合物，其中含有一种罕见的桥接酰胺键的大环基团。

  DOI：

  10.3762/bjoc.6.78

文献信息

• DESIGN, SYNTHESIS AND IN VITRO ANTI-BACTERIAL ACTIVITIES OF BENZOFURAN-ISATIN HYBRIDS
  作者：Yin-Ling WANG、Shi-Jia ZHAO、Yi LIU、Zhi XU

  DOI：10.33224/rrch/2019.64.8.6

  日期：——

  of novel benzofuran-isatin hybrids 6a-x tethered through propylene, butylene, pentylene and hexylene were designed, synthesized and evaluated for their in vitro antibacterial activities against a panel of clinically important Grampositive and Gram-negative pathogens including drug-resistant bacteria. All hybrids exhibited decent in vitro anti-bacterial activities, and the most active hybrid 6l was not

  设计，合成和评估了一系列通过丙烯，丁烯，戊烯和己烯系链的新型苯并呋喃-靛红素杂种6a-x，它们针对一系列临床上重要的革兰氏阳性和革兰氏阴性病原体（包括耐药菌）的体外抗菌活性。所有杂种均表现出良好的体外抗菌活性，活性最高的杂种6l不仅对大多数测试的革兰氏阳性菌具有与万古霉素相当的功效，而且对革兰氏阴性菌也具有很高的活性。基于以上结果，杂种6l可以作为进一步研究的线索。而且，丰富的构效关系可以为进一步优化铺平道路。
• Isatin-linked 4,4-dimethyl-5-methylene-4,5-dihydrothiazole-2-thiols for inhibition of acetylcholinesterase
  作者：Sydney M. Davis、Todd J. Eckroat

  DOI：10.1007/s00044-021-02800-y

  日期：2021.12

  Furthermore, 1b displayed non-competitive inhibition patterns in kinetic studies, whereas molecular modeling predicted a simultaneous interaction with both the CAS and PAS. In silico methods predicted several promising drug-like characteristics of 1b. Taken together, these results indicate 1b warrants further investigation as a multitarget-directed ligand for AChE inhibition.

  一系列新型靛红连接的 4,4-二甲基-5-亚甲基-4,5-二氢噻唑-2-硫醇 (IT2Ts) 1a – 1g被设计为乙酰胆碱酯酶 (AChE) 抑制剂，能够与催化活性位点 ( CAS) 和外周阴离子位点 (PAS)。目标 IT2Ts 是通过短时间合成以中等产率制备的。该系列1b和1c 中最有效的抑制剂（IC 50 分别 为 18.2 和 27.5 μM）优于利凡斯的明，并且与临床上使用的 AChE 抑制剂加兰他敏相当。此外，1b在动力学研究中显示出非竞争性抑制模式，而分子模型预测与 CAS 和 PAS 同时相互作用。计算机方法预测了1b 的几种有希望的类似药物的特征。总之，这些结果表明1b作为 AChE 抑制的多靶标配体值得进一步研究。
• Benzofuran-isatin-imine hybrids tethered via different length alkyl linkers: Design, synthesis and in vitro evaluation of anti-tubercular and anti-bacterial activities as well as cytotoxicity
  作者：Feng Gao、Tengfei Wang、Meixiang Gao、Xia Zhang、Zhuqing Liu、ShiJia Zhao、ZaoSheng Lv、Jiaqi Xiao

  DOI：10.1016/j.ejmech.2019.01.042

  日期：2019.3

  Herein we report the design and synthesis of twenty-two novel benzofuran-isatin-imine hybrids 7a-v tethered through propylene, butylene, pentylene and hexylene, and for the evaluation of their in vitro anti-tubercular and anti-bacterial activities as well as cytotoxicity. All benzofuran-isatin-imine hybrids exhibited considerable in vitro anti-TB (MIC: <0.016–0.218 μg/mL and 0.062–14.15 μg/mL against

  本文中，我们报告了通过丙烯，丁烯，戊烯和己烯系留的22种新颖的苯并呋喃-依斯丁-亚胺杂种7a-v的设计与合成，并评估了它们的体外抗结核和抗菌活性，以及细胞毒性。所有苯并呋喃靛红-亚胺杂种表现出相当大的体外抗TB（MIC：<0.016-0.218  μ克/毫升和0.062-14.15  μ克/毫升对药物敏感和MDR MTB，分别地）和抗细菌（MIC： 0.25-64  μ克/毫升和0.06-16  μ克/毫升对革兰氏阳性和革兰氏阴性菌株，分别地）的活动。它们都对VERO（CC 50）表现出可接受的细胞毒性。：8-128  μ克/毫升）。最活跃的混合7J（MIC：<0.016，0.062和0.16  μ克/毫升，分别地）是> 4.8和≥48倍以上的第一行抗结核剂有效的RIF和INH对两种药物敏感的MTBħ 37器Rv和MDR-TB分离株。此外，混合动力7J还证明有希望具有≤1MIC值抗菌活性 
• Benzofuran-isatin hybrids tethered via different length alkyl linkers and their in vitro anti-mycobacterial activities
  作者：Feng Gao、Zijian Chen、Long Ma、Lin Qiu、Jianguo Lin、Guangming Lu

  DOI：10.1016/j.bmc.2019.04.017

  日期：2019.6

  A series of novel benzofuran-isatin hybrids 6a-m tethered through different length alkyl linkers propylene, butylene, pentylene and hexylene were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against both drug-susceptible and multi-drug resistant (MDR) Mycobacterium tuberculosis (MTB) and cytotoxicity towards VERO cells. All hybrids with acceptable cytotoxicity

  设计，合成并评估了一系列通过不同长度的烷基接头拴在一起的新颖的苯并呋喃-靛红素杂化物6a-m，合成并评估了它们对药敏和耐多药（MDR）的体外抗分枝杆菌活性）结核分枝杆菌（MTB）和对VERO细胞的细胞毒性。所有在VERO细胞中具有可接受的细胞毒性的杂种（CC50：64至> 1024μg/ mL）对MIC在0.125-4μg/ mL范围内的药物敏感性和MDR-MTB菌株均表现出显着的抗分枝杆菌活性。SAR表明，接头的长度对活性起关键作用，而较长的接头可以增强活性。活性最高的杂交6d（MIC：0.125和0.125μg/ mL）与利福平（MIC：0）相当或更好。5μg/ mL）和异烟肼（MIC：0.06μg/ mL）对MTB H37Rv的抗药性比利福平（MIC：64μg/ mL）和异烟肼（MIC：> 128μg/ mL）对MDR- MTB菌株，但活性不及TAM16（MIC：针对测试的两种菌株，<0
• 7-Chloroquinoline-isatin Conjugates: Antimalarial, Antitubercular, and Cytotoxic Evaluation
  作者：Raghu Raj、Christophe Biot、Séverine Carrère-Kremer、Laurent Kremer、Yann Guérardel、Jiri Gut、Philip J. Rosenthal、Delphine Forge、Vipan Kumar

  DOI：10.1111/cbdd.12273

  日期：2014.5

  7‐chloroquinoline–isatin hybrids have been synthesized via either direct nucleophilic substitution or Cu(Ι)Cl‐mediated Mannich reaction. These new conjugates were evaluated for their antimalarial and antitubercular efficacy against a chloroquine‐resistant strain of Plasmodium falciparum and Mycobacterium tuberculosis, respectively, while the cytotoxic profiles were evaluated against 3T6 cell line, a permanent

  通过直接亲核取代或Cu（II）Cl介导的曼尼希反应，已经合成了一系列二十个由哌嗪拴系的7-氯喹啉-依斯丁杂种。分别评估了这些新的缀合物对恶性疟原虫和结核分枝杆菌的氯喹耐药菌株的抗疟和抗结核功效，同时针对永久性小鼠胚胎成纤维细胞系3T6细胞系评估了细胞毒性谱。最有效的带IC的试验化合物50 0.22  μ米针对W2株恶性疟原虫和31.62  μ米 针对胚胎成纤维细胞的细胞系（细胞毒性）显示出较高的选择性指数143.73。