3',6'-二甲氧基-[1,1':4',1''-三联苯]-2',4,4''-三醇 | 52452-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3',6'-二甲氧基-[1,1':4',1''-三联苯]-2',4,4''-三醇
• 中文别名: 三联苯曲菌素
• 英文名称: terphenyllin
• 英文别名: 3’,6’-dimethoxy-1,1’,4’,1’’-terphenyl-2’,4,4’’-triol；2,5-bis(4-hydroxyphenyl)-3,6-dimethoxyphenol
• CAS: 52452-60-5
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: YNEMPXKRLPZFAX-UHFFFAOYSA-N

物化性质

• 沸点：
  499.2±45.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2909499000
• 储存条件：
  2-8℃

制备方法与用途

生物活性

Terphenyllin 是从珊瑚源真菌念珠菌中分离得到的一种天然对三联苯代谢物，具有显著的α-葡萄糖苷酶抑制活性。

靶点：α-葡萄糖苷酶

反应信息

• 作为反应物：
  描述：

  3',6'-二甲氧基-[1,1':4',1''-三联苯]-2',4,4''-三醇 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 对羟基苯甲酸
  参考文献：
  名称：

  曲霉的有毒代谢产物的结构。I.化合物A和E，细胞毒性对三联苯。

  摘要：

  通过光谱数据、氧化反应和化合物 A 三甲基醚的合成，阐明了特征性细胞毒性化合物 A（三苯乙烯）和 E（脱氧三苯乙烯）的结构，即对三苯乙烯衍生物（1 和 24）。此外，还讨论了这些化合物及其衍生物的细胞毒性。

  DOI：

  10.1248/cpb.24.613

文献信息

• p-Terphenyls From Aspergillus sp. GZWMJZ-055: Identification, Derivation, Antioxidant and α-Glycosidase Inhibitory Activities
  作者：Yanchao Xu、Yong Wang、Dan Wu、Wenwen He、Liping Wang、Weiming Zhu

  DOI：10.3389/fmicb.2021.654963

  日期：——

  One new (1) and fifteen known (2–16) p-terphenyls were isolated from a solid culture of the endophytic fungus Aspergillus sp. GZWMJZ-055 by adding the leaves of its host Eucommia ulmoides. Furthermore, nine p-terphenyls (17–25) were synthesized from the main compounds (5–7), among which derivatives 18, 19, 21, 22, and 25 are new p-terphenyls. Compounds 15 and 16 were also, respectively, synthesized from compounds 6 and 7 by oxidative cyclization of air in the presence of silica gel. These p-terphenyls especially those with 4,2′,4″-trihydroxy (4–7, 20, 21) or 4, 4″-dihydroxy-1,2,1′,2′-furan (15, 16) substituted nucleus, exhibited significant antioxidant and α-glucosidase inhibitory activities and lower cytotoxicity to caco-2 cells. The results indicated their potential use as lead compounds or dietary supplements for treating or preventing the diabetes.

  一种内生真菌Aspergillus sp. GZWMJZ-055的固体培养物中，通过添加其寄主椴树Eucommia ulmoides的叶子，分离出一种新的（1号）和十五种已知的（2号至16号）p-三联苯。此外，从主要化合物（5号至7号）中合成了九种p-三联苯（17号至25号），其中衍生物18号、19号、21号、22号和25号是新的p-三联苯。化合物15号和16号也分别从化合物6号和7号中在硅胶存在下通过氧化环化合成。这些p-三联苯，特别是那些带有4,2′,4″-三羟基（4号至7号、20号、21号）或4,4″-二羟基-1,2,1′,2′-呋喃（15号、16号）取代核的化合物，表现出显著的抗氧化和α-葡萄糖苷酶抑制活性，并对caco-2细胞的细胞毒性较低。结果表明它们作为先导化合物或膳食补充剂，具有治疗或预防糖尿病的潜力。
• Structure‐Activity Relationships and Potent Cytotoxic Activities of Terphenyllin Derivatives from a Small Compound Library
  作者：Waqas Haider、Wei‐Feng Xu、Min Liu、Yan‐Wei Wu、Yan‐Fei Tang、Mei‐Yan Wei、Chang‐Yun Wang、Ling Lu、Chang‐Lun Shao

  DOI：10.1002/cbdv.202000207

  日期：2020.7

  A small library of 120 compounds was established with seventy new alkylated derivatives of the natural product terphenyllin, together with 45 previous reported derivatives and four natural p‐terphenyl analogs. The 70 new derivatives were semi‐synthesized and evaluated for cytotoxic activities against four cancer cell lines. Interestingly, 2′,4′′‐diethoxyterphenyllin, 2′,4,4′′‐triisopropoxyterphenyllin

  建立了一个包含 120 种化合物的小型库，其中包含 70 种新的天然产物三联苯的烷基化衍生物，以及 45 种先前报道的衍生物和四种天然对三联苯类似物。对 70 种新衍生物进行了半合成，并评估了对四种癌细胞系的细胞毒性活性。有趣的是，2',4''-二乙氧基三联苯林、2',4,4''-三异丙氧基三联苯林和2',4''-双（环戊氧基）三联苯林显示出有效的活性，IC50 值范围为0.13 至5.51 μM，与阳性对照阿霉素相似。初步的构效关系表明，引入包括乙基、烯丙基、炔丙基、异丙基、溴丙基、异戊烯基、环丙基甲基和环戊基甲基在内的烷基取代基对于提高细胞毒性很重要。
• A Terphenyllin Derivative CHNQD-00824 from the Marine Compound Library Induced DNA Damage as a Potential Anticancer Agent
  作者：Xi-Zhen Cao、Bo-Qi Zhang、Cui-Fang Wang、Jun-Na Yin、Waqas Haider、Gulab Said、Mei-Yan Wei、Ling Lu

  DOI：10.3390/md21100512

  日期：——

  need to screen and identify new agents for the effective treatment of cancer. Terphenyls—a group of aromatic hydrocarbons consisting of a linear 1,4-diaryl-substituted benzene core—has exhibited a wide range of biological activities. In this study, we discovered a terphenyllin derivative—CHNQD-00824—derived from the marine compound library as a potential anticancer agent. The cytotoxic activities of the

  随着耐药性的出现以及随之而来的高发病率和死亡率，迫切需要筛选和鉴定有效治疗癌症的新药。三联苯是一组由线性 1,4-二芳基取代的苯核心组成的芳香烃，具有广泛的生物活性。在这项研究中，我们发现了一种来自海洋化合物库的三联苯衍生物——CHNQD-00824，作为一种潜在的抗癌剂。针对 13 种不同的细胞系评估了 CHNQD-00824 化合物的细胞毒活性，IC50 值为 0.16 至 7.64 μM。进一步研究表明，CHNQD-00824 可能通过诱导 DNA 损伤来抑制癌细胞的增殖和迁移。吖啶橙染色表明 CHNQD-00824 促进斑马鱼胚胎细胞凋亡。值得注意的是，其抗癌功效在盐酸多西星（DOX）诱导的斑马鱼肝脏特异性增大模型中得到了验证。以索拉非尼作为阳性对照，CHNQD-00824 在 2.5 和 5 μM 浓度下显着抑制肿瘤生长，进一步凸显了其作为有效抗癌药物的潜力。
• Design, semisynthesis, α-glucosidase inhibitory, cytotoxic, and antibacterial activities of p-terphenyl derivatives
  作者：Xue-Qing Zhang、Xiao-Feng Mou、Ning Mao、Jie-Jie Hao、Ming Liu、Ji-Yong Zheng、Chang-Yun Wang、Yu-Cheng Gu、Chang-Lun Shao

  DOI：10.1016/j.ejmech.2018.01.057

  日期：2018.2

  Terphenyllin (1), a naturally abundant p-terphenyl metabolite, was isolated from the coral derived fungus Aspergillus candidus together with four natural analogues 2-5. To evaluate their potency and selectivity, a series of new derivatives of 1 were designed and semisynthesized. They were evaluated for their alpha-glucosidase inhibitory, cytotoxic, and antibacterial activities. Compounds 1, 3, 4, 7, 8, 10, 11, 14, 15, 21, 23, 24, 29, 39, and 40 showed significant a-glucosidase inhibitory activity with IC50 values of 4.79-15 mu M, which were stronger than that of the positive controls, 1-deoxynojirimycin (IC50 = 192.0 mu M) and acarbose (IC50 = 707,9 mu M). Compounds 7 and 10 have relatively higher therapeutic indices (CC50/IC50 = 17 and 10, respectively), representing potential promising leads. The enzyme kinetic studies of compounds I and 24 showed a non-competitive inhibition on a-glucosidase with Ki values of 1.50 and 3.45 mu M, respectively. Additionally, compounds 14, 21, 26, 29, 32, 35, and 37 were found to exhibit strong cytotoxicity against three tumor cell lines A549 (lung adenocarcinoma epithelial), HeLa (cervical carcinoma), and HepG2 (hepatocellular liver carcinoma) with IC50 values ranging from 0.15 to 5.26 mu M. Further study indicated that 32 could induce S-phase arrest in the cell cycle progression. (C) 2018 Elsevier Masson SAS. All rights reserved.
• The structures of toxic metabolites of Aspergillus candidus. I. The compounds A and E, cytotoxic p-terphenyls.
  作者：CHIKAKO TAKAHASHI、KUNITOSHI YOSHIHIRA、SHINSAKU NATORI、MAKOTO UMEDA

  DOI：10.1248/cpb.24.613

  日期：——

  The metabolites, compounds A-E, were isolated from a toxic strain of Aspergillus candidus and the structures of the characteristic cytotoxic compounds A (terphenyllin) and E (deoxyterphenyllin) were elucidated to p-terphenyl derivatives (1 and 24) by spectral data, oxidation reactions, and synthesis of compound A trimethyl ether. The cytotoxicity of the compounds and the derivatives was also discussed.

  通过光谱数据、氧化反应和化合物 A 三甲基醚的合成，阐明了特征性细胞毒性化合物 A（三苯乙烯）和 E（脱氧三苯乙烯）的结构，即对三苯乙烯衍生物（1 和 24）。此外，还讨论了这些化合物及其衍生物的细胞毒性。