n-propyl 2,4-dihydroxy-3,6-dimethylbenzoate | 261174-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: n-propyl 2,4-dihydroxy-3,6-dimethylbenzoate
• 英文别名: Propyl 2,4-dihydroxy-3,6-dimethylbenzoate
• CAS: 261174-49-6
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: WSXSVJXLDVEMLK-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C
• 沸点：
  382.5±22.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  n-propyl 2,4-dihydroxy-3,6-dimethylbenzoate 生成 3-formyl-4,6-dihydroxy-2,5-dimethyl-benzoic acid propyl ester
  参考文献：
  名称：

  Fujikawa; Nakamura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1942, vol. 62, p. 508; dtsch. Ref. S. 158

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 n-propyl 2,4-dihydroxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Fujikawa; Shimamura; Tarui, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 191,194; dtsch. Ref. S. 81

  摘要：

  DOI：

文献信息

• Activity-Guided Isolation of an Antiandrogenic Compound of<i>Pygeum africanum</i>
  作者：Sonja Schleich、Maria Papaioannou、Aria Baniahmad、Rudolf Matusch

  DOI：10.1055/s-2006-941472

  日期：2006.4

  Inactivation of the androgen receptor (AR) through androgen ablation and treatment with antiandrogens is a major goal in the therapy for prostate hyperplasia and prostate cancer. Bioactivity-directed fractionation of a selective dichloromethane extract from the stem bark of Pygeum africanum led to the isolation of the antiandrogenic compound atraric acid. Its activity was examined by an androgen receptor responsive reporter gene assay. For lead structure optimization we transformed the natural occurring compound atraric acid into its ethyl, n-propyl and n-butyl esters and their antiandrogenic activities were examined as well. In addition, benzoic acid was isolated. The structures of all compounds were determined and characterized by means of 1H- and 13C-NMR, HR-EI-mass, IR and UV spectroscopy.

  通过雄激素剥夺和抗雄激素药物治疗来灭活雄激素受体(AR)是治疗前列腺增生和前列腺癌的一个主要目标。从非洲臀果木的树皮中选择性地提取二氯甲烷，再通过生物活性引导的分离方法，得到了一种具有抗雄激素作用的化合物——刺囊酸。其活性是通过雄激素受体应答的报告基因检测方法来检测的。为了进一步优化其结构，我们将其自然界中存在的刺囊酸转化为乙酯、正丙酯和正丁酯，并检测它们的抗雄激素活性。此外，还分离出了苯甲酸。所有化合物的结构都通过1H-NMR、13C-NMR、HR-EI质谱、IR和UV光谱进行了鉴定和表征。
• Semisynthesis, Biological Evaluation and Molecular Docking Studies of Barbatic Acid Derivatives as Novel Diuretic Candidates
  作者：Xiang Yu、Yi Sui、Yinkai Xi、Yan Zhang、Guoyong Luo、Yi Long、Wude Yang

  DOI：10.3390/molecules28104010

  日期：——

  variety of biological activities. In this study, a series of esters based on barbatic acid (6a–q′) were designed, synthesized, and evaluated for their diuretic and litholytic activity at a concentration of 100 μmol/L in vitro. All target compounds were characterized using 1H NMR, 13C NMR, and HRMS, and the spatial structure of compound 6w was confirmed using X-ray crystallography. The biological results

  Barbatic acid 是一种从地衣中分离出来的化合物，具有多种生物活性。在这项研究中，设计、合成了一系列基于半巴巴酸 (6a–q') 的酯类，并评估了它们在 100 μmol/L 浓度下的体外利尿和溶石活性。使用 1H NMR、13C NMR 和 HRMS 对所有目标化合物进行了表征，并使用 X 射线晶体学确认了化合物 6w 的空间结构。生物学结果表明，包括 6c、6b' 和 6f' 在内的一些衍生物表现出强大的利尿活性，而 6j 和 6m 则表现出良好的溶石活性。分子对接研究进一步表明，6b' 与利尿相关的 WNK1 激酶具有最佳结合亲和力，而 6j 可以通过多种力量与碳酸氢盐转运蛋白 CaSR 结合。
• 一种新型坝巴酸醚类衍生物及其合成方法和应用
  申请人：贵州中医药大学

  公开号：CN116640062A

  公开（公告）日：2023-08-25

  本发明公开了一种新型坝巴酸醚类衍生物及其合成方法和应用。所述新工艺合成方法是以橡苔(2，4‑二羟基苯甲酸甲酯)作为化合物合成的起始原料，合成坝巴酸及其衍生物。本方法先合成相应的中间体酚或酸，最终再酯化缩合的方法合成缩酚酸类化合物，最终合成得到醚类化合物，有效避免了直接在酯类基础上衍生的不稳定因素，高效、方便，是适合缩酚酸类化合物合成的有效途径。通过MTT法检测细胞毒性实验，该醚类化合物均对MDCK细胞具有毒性，对癌细胞A549、HePG2和22RV1具有细胞毒性，说明具有潜在的抗肿瘤活性，对于治疗抗肿瘤性疾病具有重要意义。
• Fujikawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 473,477; dtsch. Ref. S. 177
  作者：Fujikawa

  DOI：——

  日期：——
• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid
  作者：Sunil Kumar KC、Klaus Müller

  DOI：10.1016/s0223-5234(99)00132-4

  日期：1999.12

  A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range. (C) 1999 Editions scientifiques et medicales Elsevier SAS.