NSC 117272

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: NSC 117272
• 英文别名: 3,3'-((2,4-dichlorophenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione)
• 化学式: C₂₇H₁₄Cl₂O₆
• 分子量: 505.311
• InChiKey: XOTNZDGXFOVGTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  108.74
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 NSC 117272 在 吡啶 、 锌 作用下， 反应 72.0h， 以97%的产率得到3,3’-(2,4-dichlorophenylmethylene)bis(naphthalene-1,2,4-triyl triacetate)
  参考文献：
  名称：

  Inhibition of Zika Virus Replication by Synthetic Bis-Naphthoquinones

  摘要：

  Zika virus (ZIKV) is a mosquito-borne pathogen which is a current global public health concern. There are currently no approved vaccines or antivirals against ZIKV infection. Taking into account that naphthoquinones have shown promising antiviral activity, the aim of this study was to describe the screening of two bis-naphthoquinones series against ZIKV. Twenty seven compounds were evaluated against ZIKV using Vero cells. The findings showed that among the compounds analyzed four were promising. Compound 3.3' -((2-nitrophenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione) containing the nitro group at the ortho position showed the best selectivity index, followed by compound 3,3'-(4-chlorophenylmethylene)bis(naphthalene-1,2,4-triyl triacetate) with the chlorophenylmethylene radical. These results demonstrate that these bis-naphthoquinones are largely effective in inhibiting the replication of ZIKV.

  DOI：

  10.21577/0103-5053.20190071
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 2,4-二氯苯甲醛 在 N,N,N',N'-tetramethylethylenediammonium sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以85%的产率得到NSC 117272
  参考文献：
  名称：

  高效和绿色的协议，用于合成3,3'-（芳基亚甲基）-双（2-羟基萘醌）衍生物，通过特殊的熔融盐催化

  摘要：

  合成3,3'-（芳基亚甲基）-双（2-羟基萘醌）{3,3'-（芳基亚甲基）-双（2-羟基萘-1,4-二酮）}衍生物的高效且绿色协议具有已开发。2-羟基萘醌（2-羟基萘-1,4-二酮）（2当量）与芳醛（1当量）在熔融金属盐N，N，N'，N'-四甲基乙烯二铵双-存在下的反应在无溶剂条件下，硫酸氢盐（[TMEDAH 2] [HSO 4] 2）以高收率和相对短的反应时间提供了所述化合物。

  DOI：

  10.1515/znb-2020-0174

文献信息

• Highly efficacious preparation of 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives catalyzed by a nanorod-structured organic–inorganic hybrid material
  作者：Abdolkarim Zare、Jaleh Atashrooz、Mohammad Mehdi Eskandari

  DOI：10.1007/s11164-020-04375-6

  日期：2021.4

  catalyst for the solvent-free preparation of 3,3'-(arylmethylene)-bis(2-hydroxynaphthoquinone) 3,3′-(arylmethylene)-bis(2-hydroxynaphthalene-1,4-dione)} derivatives in high yields and relatively short times. The one-pot pseudo-multi-component reaction of 2-hydroxynaphthoquinone (2-hydroxynaphthalene-1,4-dione) (2 eq.) and arylaldehydes (1 eq.) has been used for the preparation of these compounds. Graphic

  摘要 纳米棒结构的有机-无机杂化材料，即纳米棒-[SiO 2 -Pr -Im-SO 3 H] [CF 3 CO 2 ]（N- [SPIS] [TFA]）已被用作高效，双重的无溶剂制备3,3'-（芳基亚甲基）-双（2-羟基萘醌）3,3'-（芳基亚甲基）-双（2-羟基萘-1,4-二酮）}的功能性和可回收催化剂衍生产品，收益高且时间短。2-羟基萘醌（2-羟基萘-1,4-二酮）（2eq。）和芳醛（1eq。）的一锅法假多组分反应已用于制备这些化合物。 图形摘要
• Selective Pro-Apoptotic Activity of Novel 3,3′-(Aryl/Alkyl-Methylene)Bis(2-Hydroxynaphthalene-1,4-Dione) Derivatives on Human Cancer Cells via the Induction Reactive Oxygen Species
  作者：Pritam Sadhukhan、Sukanya Saha、Krishnendu Sinha、Goutam Brahmachari、Parames C. Sil

  DOI：10.1371/journal.pone.0158694

  日期：——

  compared to cisplatin, thus indicating the superiority of 1j as a possible anticancer agent. This compound was observed to induce apoptosis in the glioma cells by inducing the caspase dependent apoptotic pathways via ROS and downregulating the PI3K/AKT/mTOR pathway. Estimation of different oxidative stress markers also confirms the induction of oxidative stress in 1j exposed cancer cells. The toxicity of 1j

  除了正常细胞之外，选择性诱导癌细胞凋亡被认为是对抗癌症的有效策略。在本研究中，分析了一系列二十二 (22) 种合成 3,3'-(芳基/烷基亚甲基)双(2-羟基萘-1,4-二酮)双劳松衍生物的促凋亡作用使用 MTT 测定在六种不同细胞系（五种癌性细胞系和一种正常细胞系）中检测活性。在这 22 种测试化合物中，1j 在研究中使用的不同细胞系中诱导人神经胶质瘤细胞 (CCF-4) 凋亡最有效。然后将该化合物 1j 的活性与流行的抗癌药物顺铂进行比较，顺铂因其肾毒性而使用有限。在这项研究中，与顺铂相比，1j 衍生物对正常肾细胞的毒性要小得多，从而表明 1j 作为一种可能的抗癌药物的优越性。据观察，该化合物通过 ROS 诱导 caspase 依赖性细胞凋亡途径并下调 PI3K/AKT/mTOR 途径，从而诱导神经胶质瘤细胞凋亡。对不同氧化应激标记物的估计也证实了 1j 暴露的癌细胞中氧化应激的诱导。
• Camphor sulfonic acid catalyzed facile and general method for the synthesis of 3,3'-(arylmethylene)<i>bis</i>(4-hydroxy-2<i>H</i>-chromen-2-ones), 3,3'-(arylmethylene)<i>bis</i>(2-hydroxynaphthalene-1,4-diones) and 3,3'-(2-oxoindoline-3,3-diyl)<i>bis</i>(2-hydroxynaphthalene-1,4-dione) derivatives at room temperature
  作者：Gurpreet Kaur、Diksha Singh、Arvind Singh、Bubun Banerjee

  DOI：10.1080/00397911.2020.1856877

  日期：2021.4.3

  sulfonic acid catalyzed a straightforward, efficient, and general method has been developed for the synthesis of 3,3'-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones), 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4-diones) and 3,3'-(2-oxoindoline-3,3-diyl)bis(2-hydroxynaphthalene-1,4-dione) derivatives in aqueous ethanol at room temperature from the reactions of various aromatic aldehydes and 4-hydroxycoumarin

  摘要 已开发出樟脑磺酸催化的简单，有效且通用的方法，用于合成3,3'-（芳基亚甲基）双（4-羟基-2 H-铬烯-2-酮），3,3'-（芳基亚甲基））在室温下于室温下在乙醇水溶液中生成双（2-羟基萘-1,4-二酮）和3,3'-（2-氧代吲哚-3,3-二基）双（2-羟基萘-1,4-二酮）衍生物各种芳香醛与4-羟基香豆素或2-羟基萘-1,4-二酮的反应。温和的反应条件，使用无金属的有机催化剂，良好或优异的收率，高原子经济性，对环境无害，产物易于分离以及无需柱色谱分离是该开发方案的一些主要优点。
• Inhibition of Zika Virus Replication by Synthetic Bis-Naphthoquinones
  作者：Daniel Gonzaga、Rafaela Gomes、Roberta Marra、Fernando da Silva、Max Gomes、Davis Ferreira、Raissa Santos、Ana Pinto、Norman Arthur Ratcliffe、Claudio Cirne-Santos、Caroline Barros、Vitor Ferreira、Izabel Christina Paixão

  DOI：10.21577/0103-5053.20190071

  日期：——

  Zika virus (ZIKV) is a mosquito-borne pathogen which is a current global public health concern. There are currently no approved vaccines or antivirals against ZIKV infection. Taking into account that naphthoquinones have shown promising antiviral activity, the aim of this study was to describe the screening of two bis-naphthoquinones series against ZIKV. Twenty seven compounds were evaluated against ZIKV using Vero cells. The findings showed that among the compounds analyzed four were promising. Compound 3.3' -((2-nitrophenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione) containing the nitro group at the ortho position showed the best selectivity index, followed by compound 3,3'-(4-chlorophenylmethylene)bis(naphthalene-1,2,4-triyl triacetate) with the chlorophenylmethylene radical. These results demonstrate that these bis-naphthoquinones are largely effective in inhibiting the replication of ZIKV.
• A highly efficient and green protocol for the synthesis of 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) derivatives catalyzed by a dicationic molten salt
  作者：Abdolkarim Zare、Aysoda Ghobadpoor

  DOI：10.1515/znb-2020-0174

  日期：2021.2.23

  A highly efficient and green protocol for the synthesis of 3,3′-(arylmethylene)-bis(2-hydroxynaphthoquinone) 3,3′-(arylmethylene)-bis(2-hydroxynaphthalene-1,4-dione)} derivatives has been developed. The reaction of 2-hydroxynaphthoquinone (2-hydroxynaphthalene-1,4-dione) (2 eq.) and arylaldehydes (1 eq.) in the presence of the dicationic molten salt N , N , N ′, N ′-tetramethylethylenediaminium bis-hydrogensulfate

  合成3,3'-（芳基亚甲基）-双（2-羟基萘醌）3,3'-（芳基亚甲基）-双（2-羟基萘-1,4-二酮）}衍生物的高效且绿色协议具有已开发。2-羟基萘醌（2-羟基萘-1,4-二酮）（2当量）与芳醛（1当量）在熔融金属盐N，N，N'，N'-四甲基乙烯二铵双-存在下的反应在无溶剂条件下，硫酸氢盐（[TMEDAH 2] [HSO 4] 2）以高收率和相对短的反应时间提供了所述化合物。