1H-吲哚-2,3-二酮,1-[(4-硝基苯基)甲基]- | 31541-33-0

• 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
• 中文名称: 1H-吲哚-2,3-二酮,1-[(4-硝基苯基)甲基]-
• 英文名称: 1-(4-nitro-benzyl)-indoline-2,3-dione
• 英文别名: 1-(4-nitrobenzyl)-1H-indole-2,3-dione；1-[(4-nitrophenyl)methyl]indole-2,3-dione
• CAS: 31541-33-0
• 化学式: C₁₅H₁₀N₂O₄
• mdl: MFCD00224236
• 分子量: 282.255
• InChiKey: FGSNEAMVFHNNKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1H-吲哚-2,3-二酮,1-[(4-硝基苯基)甲基]- 在 六乙基亚磷酸胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到1,1'-bis(4-nitrobenzyl)-3,3'-bi(1H-indolylidene)-2,2'-dione
  参考文献：
  名称：

  Regiochemistry of Deoxygenation of Nitro-Containing Isatins with Tris(diethylamino)phosphine

  摘要：

  Isatin derivatives containing a 4-nitrophenyl group in the side chain or a nitro group in the aromatic fragment reacted with tris(diethylamino)phosphine to give the corresponding isoindigo derivatives with high yields and chemoselectivity.

  DOI：

  10.1134/s1070363218110087
• 作为产物：
  描述：

  4-硝基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 potassium iodide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 6.0h， 生成 1H-吲哚-2,3-二酮,1-[(4-硝基苯基)甲基]-
  参考文献：
  名称：

  De novo design and synthesis of HIV-1 integrase inhibitors

  摘要：

  Existing AIDS therapies are out of reach for most HIV-infected people in developing countries and, where available, they are limited by their toxicity and their cost. New anti-HIV agents are needed urgently to combat emerging viral resistance and reduce the side effects associated with currently available drugs. Toward this end, LeapFrog, a de novo drug design program was used to design novel, potent, and selective inhibitors of HIV-1 integrase. The designed compounds were synthesized and tested for in vitro inhibition of HIV-1 integrase. Out of the 25 compounds that were designed, and synthesized, four molecules (compounds 23, 26, 43, and 59) showed moderate to low inhibition of HIV-1 integrase for 3'-processing and 3'-strand transfer activities. Nonetheless, these compounds possess structural features not seen in known HIV-1 integrase inhibitors and thus can serve as excellent leads for further optimization of anti-HIV-1 integrase activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.005

文献信息

• Identification and further development of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B
  作者：Viktor V. Vintonyak、Karin Warburg、Björn Over、Katja Hübel、Daniel Rauh、Herbert Waldmann

  DOI：10.1016/j.tet.2011.04.026

  日期：2011.9

  biologically active component. The reported MptpB inhibitors show excellent selectivity against a selected panel of protein tyrosine phosphatases, including MptpA (M. tuberculosis protein tyrosine phosphatase A), PTP1B (protein tyrosine phosphatase 1B), SHP-2 (Src homology 2 domain-containing protein tyrosine phosphatase), PTPN2, h-PTPβ (human protein tyrosine phosphatase β), and VHR (Vaccinia virus VH1-related

  结核病仍然是全世界发病率和死亡率的主要原因。从蛋白酪氨酸磷酸酶结核分枝杆菌是由于它们在细胞内生存发展的作用在对抗结核病的新策略有吸引力的目标结核分枝杆菌的各种感染模型。在这里，我们报道了与吲哚啉酮-2螺环稠合的噻唑烷酮类化合物的鉴定和进一步开发，这是一类新型的结核分枝杆菌蛋白酪氨酸磷酸酶B的有效和选择性抑制剂。详细的结构-活性关系（SAR）研究表明：硝基取代的2-氧吲哚核与二卤代苯胺和卤代N-苄基部分对于针对MptpB（结核分枝杆菌蛋白酪氨酸磷酸酶B）的强抑制活性是必不可少的。所鉴定化合物的小结构修饰导致化合物溶解度和细胞渗透性的显着改善，从而在微摩尔范围内保持抑制活性。发现螺中心的构型对于抑制活性是至关重要的，并且外消旋物的分离显示出R -（-）-对映异构体是生物活性成分。报道的MptpB抑制剂对选定的一组蛋白酪氨酸磷酸酶（包括MptpA（结核分枝杆菌）蛋白酪氨酸磷酸酶A），PTP1B（
• Design, synthesis,<i>in silico</i>molecular modelling studies and biological evaluation of novel indole-thiazolidinedione hybrid analogues as potential pancreatic lipase inhibitors
  作者：Ginson George、Prashant S. Auti、Atish T. Paul

  DOI：10.1039/d0nj05649a

  日期：——

  inhibitory activity (IC50 – 7.30 and 9.51 μM, respectively). Kinetic study of these potent analogues revealed their competitive mode of enzyme inhibition. This fact was confirmed via fluorescence spectroscopy which further suggested the presence of one binding site for the synthesized analogues. Molecular docking of the synthesized analogues was performed using human PL (PDB ID: 1LPB). The obtained MolDock

  胰腺脂肪酶（PL）是负责饮食中甘油三酸酯消化的关键酶。因此，其抑制被认为是肥胖的管理和/或治疗的有希望的靶标。使用分子杂交方法合成了一系列新的吲哚-噻唑烷二酮（TZD）杂交类似物，并通过PL抑制评估了它们的抗肥胖作用。在甲醇中存在KOH水溶液的情况下，通过各种取代的Isatin与TZD之间的缩合反应，合成了目标类似物。在合成的类似物中，7k和7m表现出潜在的PL抑制活性（IC 50–分别为7.30和9.51μM）。这些有效类似物的动力学研究揭示了其竞争性的酶抑制方式。通过荧光光谱证实了这一事实，该荧光光谱进一步表明了合成的类似物的一个结合位点的存在。使用人类PL（PDB ID：1LPB）进行合成类似物的分子对接。获得的MolDock得分与体外PL抑制活性一致（Pearson r = 0.9108，p<0.05）。此外，1LPB-配体的稳定构象表明这些复合物在动态环境中的稳定性。这些研究为吲
• Zinc-Mediated C-3 α-Prenylation of Isatins with Prenyl Bromide: Access to 3-Prenyl-3-hydroxy-2-oxindoles and Its Application
  作者：Li-Ming Zhao、Ai-Li Zhang、Jie-Huan Zhang、Hua-Shuai Gao、Wei Zhou

  DOI：10.1021/acs.joc.6b00836

  日期：2016.7.1

  A convenient and highly α-regioselective strategy for the synthesis of 3-prenyl-3-hydroxy-2-oxindoles has been developed starting from isatins and prenylzinc with good to excellent yields. This protocol provides a straightforward and practical way to introduce an α-prenyl moiety into the C-3 position of isatins. The advantages of this reaction are use of the cheap and readily available reagents, operational

  从靛红和异戊烯基锌开始，已经开发了一种方便且高度α-区域选择性的合成3-异戊烯基-3-羟基-2-氧吲哚的策略，其收率良好。该方案提供了将α-异戊二烯基部分引入靛红的C-3位的直接而实用的方法。该反应的优点是使用便宜且容易获得的试剂，操作简便和底物范围广。此外，该转化被应用于几种含羟吲哚的天然产物的合成，这进一步证明了该方法的合成效用。
• Discovery of natural product-like spirooxindole derivatives as highly potent and selective LSD1/KDM1A inhibitors for AML treatment
  作者：Chao Yang、Yuan Fang、Xiang Luo、Dehong Teng、Zhongqiu Liu、Yingtang Zhou、Guochao Liao

  DOI：10.1016/j.bioorg.2022.105596

  日期：2022.3

  natural LSD1 inhibitor higenamine, we herein performed further structure-based design, synthesis, and extensive structure–activity relationship (SAR) studies, affording structurally new spirooxindole derivatives. Particularly, FY-56 was identified to be a highly potent LSD1 inhibitor (IC50 = 42 nM) and showed high selectivity over monoamine oxidases (MAO-A/B). Mechanistic studies showed that FY-56 moderately

  组蛋白赖氨酸特异性去甲基化酶 1 (LSD1) 是一种很有前途的癌症治疗新靶点。在发现天然 LSD1 抑制剂去甲素后，我们在此进行了进一步的基于结构的设计、合成和广泛的构效关系 (SAR) 研究，提供了结构上新的螺氧吲哚衍生物。特别是，FY-56 被鉴定为一种高效的 LSD1 抑制剂（IC 50 = 42 nM) 并显示出对单胺氧化酶 (MAO-A/B) 的高选择性。机制研究表明，FY-56 适度抑制白血病细胞的增殖和克隆形成，诱导 H3K4me1/2 积累和 p53 活化，并降低转录因子 HOXA9 和 MEIS1 的 mRNA 水平。同时，FY-56 诱导 MOLM-13 和 MV4-11 细胞的分化，伴随着分化巨噬细胞和单核细胞特征性标志物的百分比增加。进一步的体内研究表明，FY-56 明显降低 CD45 + /CD33 +的比例外周血和脾脏中的白细胞，显着延长小鼠的存活率。总的来说，FY-56
• One step access to oxindole-based β-lactams through Ugi four-center three-component reaction
  作者：Giulia Rainoldi、Giordano Lesma、Claudia Picozzi、Leonardo Lo Presti、Alessandra Silvani

  DOI：10.1039/c8ra08165d

  日期：——

  A multicomponent Ugi reaction involving isatin, isocyanide and β-amino acid components has been developed. The reactions proceeded smoothly to give β-lactam-containing 3,3-disubstituted oxindoles in only one step and generally high yields. When chiral, non racemic, β-amino acids were used, products were obtained as enantiomerically pure β-lactams diastereoisomers, whose relative stereochemistry was

  已开发出涉及靛红、异氰化物和 β-氨基酸组分的多组分 Ugi 反应。反应顺利进行，仅需一步即可得到含β-内酰胺的3,3-二取代羟吲哚类化合物，收率普遍较高。当使用手性、非外消旋的 β-氨基酸时，得到的产物为对映体纯的 β-内酰胺非对映异构体，其相对立体化学通过 X 射线分析确定。对于一种化合物，初步强调了其较弱的抗菌活性。