1-[(2-硝基苯基)甲基]吲哚-2,3-二酮 | 151383-69-6

• 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: 1-[(2-硝基苯基)甲基]吲哚-2,3-二酮
• 英文名称: 1-(2-nitrobenzyl)indoline-2,3-dione
• 英文别名: 1H-Indole-2,3-dione, 1-[(2-nitrophenyl)methyl]-；1-[(2-nitrophenyl)methyl]indole-2,3-dione
• CAS: 151383-69-6
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: DOYKNAFJCIFMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  1-[(2-硝基苯基)甲基]吲哚-2,3-二酮 在 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以76%的产率得到1-(2-nitrobenzyl)-5-bromoindole-2,3-dione
  参考文献：
  名称：

  Baiocchi; Giannangeli; Rossi, Il Farmaco, 1993, vol. 48, # 4, p. 487 - 501

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基硝基苯 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 16.0h， 生成 1-[(2-硝基苯基)甲基]吲哚-2,3-二酮
  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

• Synthesis of Carbamoyl Fluorides via a Selective Fluorinative Beckmann Fragmentation
  作者：Jin Woo Song、Hee Nam Lim

  DOI：10.1021/acs.orglett.1c01721

  日期：2021.7.16

  useful carbamoyl fluorides. High selectivity for fragmentation over a potentially competing Beckmann rearrangement was observed. This protocol has a distinct mechanism and thus a different substrate scope compared with other synthetic methods. α-Oximinoamides derived from the readily available secondary amines, lactams, or isatins were converted into structurally diverse carbamoyl fluorides.

  α-肟基酰胺的氟化贝克曼片段被设计为提供合成有用的氨基甲酰氟。观察到对潜在竞争性贝克曼重排的高断裂选择性。与其他合成方法相比，该协议具有独特的机制，因此具有不同的底物范围。源自易得的仲胺、内酰胺或靛红的 α-肟基酰胺被转化为结构多样的氨基甲酰氟。
• Grandolini, Giuliano; Ambrogi, Valeria; Perioli, Luana, Il Farmaco, 1997, vol. 52, # 11, p. 678 - 684
  作者：Grandolini, Giuliano、Ambrogi, Valeria、Perioli, Luana、Giannangeli, Marilena、Jovicevic, Ljuba、Rossi, Vilma

  DOI：——

  日期：——
• [EN] N-[(AMINOSULFONYL)PHENYL]-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-HYDRAZINECARBOTHIOAMIDE DERIVATIVES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS<br/>[FR] DÉRIVÉS DE N-[(AMINOSULFONYL)PHÉNYL]-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDÈNE)-HYDRAZINECARBOTHIOAMIDE POUR LE TRAITEMENT DU CANCER ET DE TROUBLES IMMUNOLOGIQUES
  申请人：ISTANBUL UNIV REKTORLUGU

  公开号：WO2017099695A1

  公开（公告）日：2017-06-15

  N-[(aminosulfonyl)phenyl]-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-hydrazinecarbothioamide derivatives of the following formula (III) for treating cancer and immunological disorders. R5, R6 and R7 are each independently selected from hydrogen and a sulfonamide group, provided that at least one of R5, R6 or R7 is a sulfonamide group. The substituents R1 to R4 are each independently either hydrogen or one of the substituents defined in the claims.
• De novo design and synthesis of HIV-1 integrase inhibitors
  作者：Mahindra T Makhija、Rajesh T Kasliwal、Vithal M Kulkarni、Nouri Neamati

  DOI：10.1016/j.bmc.2004.02.005

  日期：2004.5

  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.
• Baiocchi; Giannangeli; Rossi, Il Farmaco, 1993, vol. 48, # 4, p. 487 - 501
  作者：Baiocchi、Giannangeli、Rossi、Ambrogi、Grandolini、Perioli

  DOI：——

  日期：——