diospyrin dimethyl ether | 39093-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diospyrin dimethyl ether
• 英文别名: Diospyrindimethylaether；Diospyrin, dimethyl ether；5-methoxy-6-(5-methoxy-7-methyl-1,4-dioxonaphthalen-2-yl)-7-methylnaphthalene-1,4-dione
• CAS: 39093-14-6
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: PEHFVNNNUFIZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diospyrin dimethyl ether 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到柿双醌
  参考文献：
  名称：

  Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases

  摘要：

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.

  DOI：

  10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i
• 作为产物：
  描述：

  2-溴-5-羟基-7-甲基-1,4-萘醌 在 四(三苯基膦)钯 ammonium cerium(IV) nitrate 、 sodium carbonate 、 silver(l) oxide 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 4.83h， 生成 diospyrin dimethyl ether
  参考文献：
  名称：

  Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases

  摘要：

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.

  DOI：

  10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i

文献信息

• Ebenaceae extractives. Part III. Binaphthaquinones from Diospyros species
  作者：A. L. Fallas、R. H. Thomson

  DOI：10.1039/j39680002279

  日期：——

  Diospyrin and isodiospyrin have been isolated from the bark of Diospyros mespiliformis. Isodiospyrin was also found in the bark and wood of D. virginiana. Isodiospyrin is optically active and, like diospyrin, is an unsymmetrical dimer of 7-methyljuglone, the two naphthaquinone moieties being coupled at C-6 and C-8′. The bark of D. elliptifolia contains betulin, lupeol, plumbagin (2-methyljuglone),

  从柿（Diospyros mespiliformis）的树皮中分离出了薯and和异嘧啶。在弗吉尼亚丁香（D. virginiana）的树皮和木材中也发现了异嘧啶。异嘧啶具有光学活性，并且与薯精一样，是7-甲基ju酮的不对称二聚体，两个萘醌部分在C-6和C-8'处偶联。D. elliptifolia的树皮中含有桦木素，羽扇豆酚，羽扇豆蛋白（2-甲基juglone）和另一种二聚体Elliptinone，其与薯os甙和异薯py甙同分异构。Elliptinone具有6,6'-双酚苄青霉素的结构。
• Novel glycoconjugates of diospyrin, a quinonoid plant product: synthesis and evaluation of cytotoxicity against human malignant melanoma (A375) and laryngeal carcinoma (Hep2)
  作者：Madhushree Das Sarma、Rina Ghosh、Amarendra Patra、Rajdeep Chowdhury、Keya Chaudhuri、Banasri Hazra

  DOI：10.1039/b707851j

  日期：——

  Glycoside derivatives of diospyrin (1) were synthesized for the first time, and the cytotoxicity of the novel compounds vis-à-vis their precursors were evaluated against two human cancer cell lines, viz. malignant melanoma (A375) and laryngeal carcinoma (Hep2). The IC50 values were in the low micromolar range for all the compounds tested, and A375 cells showed comparatively greater sensitivity than Hep2. Most of the compounds exhibited enhanced activity as compared to the plant-derived quinonoid precursor of the series (1), while the aminophenyl mannosyl (6) was found to be the most effective derivative. In A375 cells, 6 (IC50 = 0.02 µM) showed the maximum increase in cytotoxicity (∼35-fold) over that of 1 (IC50 = 0.82 µM). Again, when the glycosides were evaluated at a given concentration (0.1 µM) for their relative capacity to generate ROS from A375 cells, the compound 6 could produce the highest amount of ROS. Incidentally, this derivative also showed a comparatively lower toxicity (IC50 ∼ 41 µM) when tested against normal human peripheral blood mononuclear cells, indicating a fair prospect of its development as a novel chemotherapeutic agent for the treatment of malignant melanoma.

  研究人员首次合成了二OSpyrin（1）的糖苷衍生物，并评估了这些新型化合物相对于其前体对两种人类癌细胞系（即恶性黑色素瘤（A375）和喉癌（Hep2））的细胞毒性。所有受试化合物的 IC50 值都在低微摩尔范围内，A375 细胞比 Hep2 细胞表现出更高的敏感性。与该系列中源自植物的醌类化合物前体（1）相比，大多数化合物的活性都有所增强，而氨基苯基甘露糖苷（6）被认为是最有效的衍生物。在 A375 细胞中，6（IC50 = 0.02 µM）比 1（IC50 = 0.82 µM）的细胞毒性增加最多（35 倍）。同样，在给定浓度（0.1 µM）下评估苷类化合物产生 A375 细胞 ROS 的相对能力时，化合物 6 产生的 ROS 量最高。顺便提一下，在对正常人外周血单核细胞进行测试时，这种衍生物也显示出相对较低的毒性（IC50 ∼ 41 µM），这表明它有望发展成为一种新型化疗药物，用于治疗恶性黑色素瘤。
• Synthesis and antiproliferative activity of some novel derivatives of diospyrin, a plant-derived naphthoquinonoid
  作者：Madhushree Das Sarma、Rina Ghosh、Amarendra Patra、Banasri Hazra

  DOI：10.1016/j.bmc.2007.03.050

  日期：2007.6.1

  Derivatisation of diospyrin, a bisnaphthoquinonoid isolated from Diospyros montana Roxb., led to the modification of its inhibitory activity, in vitro, towards a murine tumour model, Ehrlich ascites carcinoma (EAC), and two human cancer cell lines, viz., malignant skin melanoma (A375) and epidermoid laryngeal carcinoma (Hep2). Among the novel derivatives, an epoxide exhibited the maximum antiproliferative

  洋地黄（Diospyros montana Roxb。）分离出的一种双萘并醌类化合物地鬼臼毒的衍生化，导致其对鼠肿瘤模型，艾氏腹水癌（EAC）和两种人类癌细胞系（即恶性皮肤）的抑制活性发生了改变。黑色素瘤（A375）和表皮样喉癌（Hep2）。在新型衍生物中，环氧化物在正常人外周血单核细胞（PBMC）中表现出最大的抗增殖活性（IC（50）值在0.03-0.21 microM范围内）和相​​对较低的毒性（IC（50）约98 microM）。 ）。该化合物可能为临床开发有效的抗癌抗癌药物提供新的“线索”。
• Synthesis of novel aminoquinonoid analogues of diospyrin and evaluation of their inhibitory activity against murine and human cancer cells
  作者：Madhushree Das Sarma、Rina Ghosh、Amarendra Patra、Banasri Hazra

  DOI：10.1016/j.ejmech.2007.11.028

  日期：2008.9

  The synthesis and tumor-inhibitory activity of a series of aminonaphthoquinone derivatives of diospyrin, which was isolated from Diospyros montana Roxb., are presented here for the first time. An aminoacetate derivative showed the maximum (approximately 93%) increase in life span in vivo against murine Ehrlich ascites carcinoma (EAC) at a dose of 1 mg kg(-1)day(-1) (ip; five doses), and the lowest

  首次从Diospyros montana Roxb。中分离出的一系列Diospyrin氨基萘醌衍生物的合成和抑瘤活性。氨基乙酸衍生物在1 mg kg（-1）day（-1）（ip; 5剂）剂量下对鼠艾氏腹水癌（EAC）的体内寿命最大（约93％）增加，并且体外最低IC50（0.06 microM）。此外，当针对人细胞系进行评估时，相同的类似物还显示出抗增殖活性的显着增强，即。恶性皮肤黑素瘤和表皮样喉癌（分别为IC50 = 0.06和0.92 microM）与天然前驱体薯os素（分别为IC50 = 0.82和3.58 microM）相比。而且，与正常人淋巴细胞相比，发现薯os苷及其所有衍生物对肿瘤细胞显示出明显更大的细胞毒性（约17到1441倍）。所有这些醌类化合物在EAC细胞中产生了大量的活性氧，或多或少与其各自的IC50值相当。
• Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
  作者：Glenn A. Pullella、Daniel Vuong、Ernest Lacey、Matthew J. Piggott

  DOI：10.1021/acs.jnatprod.0c00800

  日期：2020.12.24

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.