ocimarin | 10185-02-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ocimarin
• 英文别名: 7-hydroxy-3-(2-hydroxyethyl)-4-methyl-2H-1-benzopyran-2-one；3-(β-Hydroxyaethyl)-7-hydroxy-4-methylcoumarin；7-Hydroxy-4-methyl-3-(2-hydroxy-ethyl)-cumarin；7-hydroxy-3-(2-hydroxy-ethyl)-4-methyl-chromen-2-one；7-Hydroxy-4-methyl-3-(2-hydroxy-ethyl)coumarin；7-hydroxy-3-(2-hydroxyethyl)-4-methylchromen-2-one
• CAS: 10185-02-1
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: VCGFYFKJZGIZMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  ocimarin 、 茄呢醇溴化物 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 7-solanesyloxy-3-(2-hydroxy-ethyl)-4-methyl-chromen-2-one
  参考文献：
  名称：

  Novel class of hybrid natural products as antidiabetic agents

  摘要：

  A number of O-alkylated xanthone, carbazoles and coumarins have been synthesised and screened for their in vitro anti-diabetic activity, such as glucose-6-phosphatase, glycogen phosphorylase and alpha glucosidase inhibitors. Compounds which were showing significant percentage inhibition were also tested for in vivo anti-hyperglycemic activity in sucrose loaded normal and streptozotocin (STZ)-induced diabetic rats. These compounds show 22.1, 24.4 and 26.7% and 20.8, 25.0, 20.5% lowering in sucrose loaded normal rats and STZ-induced diabetic rats at a dose of 100 mg kg-1.

  DOI：

  10.1080/14786410701824940
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 、 间苯二酚 在 silica supported boric trisulfuric anhydride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以90%的产率得到ocimarin
  参考文献：
  名称：

  二氧化硅负载的硼酸三硫酸酐作为一种新型高效催化剂，用于通过 Pechmann 缩合无溶剂合成香豆素

  摘要：

  结果表明，二氧化硅负载的三硫酸硼酸酐 (BTSA.SiO 2) 是一种新型、合适且通用的催化剂，可在温和且无溶剂的条件下通过 Pechmann 环缩合反应高效清洁合成香豆素。不同种类的酚类和β-酮酯进行环化反应。特别是，这种催化剂使活性较低的酚类的缩合变得可行。除了所描述的好处之外，所报道的催化剂还成功地用于从 3-乙酰二氢呋喃-2(3 H)-one 和雌二醇（性激素）合成新型香豆素。

  DOI：

  10.3998/ark.5550190.0013.910

文献信息

• Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition
  作者：Marjaneh Samadizadeh、Saeed Nouri、Faeze Kiani Moghadam

  DOI：10.1007/s11164-016-2447-5

  日期：2016.6

  functionalization of magnetic nanoparticles. This new catalyst was prepared using the reaction between magnetic nanoparticles and sodium 2-bromoethane-1-sulfonate. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA) was found as efficient catalyst for the synthesis of coumarin derivatives using Pechmann condensation under mild condition. This reaction was catalyzed by MNESA under solvent-free

  本文报道了一种基于磁性纳米粒子磺酸功能化的高效多相催化剂。该新型催化剂是利用磁性纳米粒子与2-溴乙烷-1-磺酸钠之间的反应制备的。发现磁性纳米粒子官能化的乙烷磺酸（MNESA）是在温和条件下使用Pechmann缩合合成香豆素衍生物的有效催化剂。在90°C无溶剂条件下，通过MNESA催化该反应，从而以优异的收率得到相应的产物。催化剂容易从反应条件中分离出来，并且在活性一致的情况下可以重复使用多次。
• Constituents of <i>Ocimum sanctum</i> with Antistress Activity
  作者：Prasoon Gupta、Dinesh Kumar Yadav、Kiran Babu Siripurapu、Guatam Palit、Rakesh Maurya

  DOI：10.1021/np0700164

  日期：2007.9.1

  Three new compounds, ocimumosides A (1) and B (2) and ocimarin (3), were isolated from an extract of the leaves of holy basil (Ocimum sanctum), together with eight known substances, apigenin, apigenin-7-O-beta-D-glucopyranoside, apigenin-7-O-beta-D-glucuronic acid (4), apigenin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucopyranoside, luteolin-5-O-beta-D-glucopyranoside, and 4-allyl-1-O-beta-D-glucopyronosyl-2-hydroxybenzene (5), and two known cerebrosides. The structures of the new compounds were determined on the basis of extensive 1D and 2D NMR spectroscopic analysis. The new compounds (1-3) and the known compounds 4 and 5 were screened at a dose of 40 mg/kg body weight for acute stress-induced biochemical changes in male Sprague-Dawley rats. Compound 1 displayed promising antistress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 2 and 5 were also effective in normalizing most of these stress parameters. In contrast, compounds 3 and 4 were ineffective in normalizing any of these effects.
• First total synthesis of ocimarin
  作者：Jin Hui Yang、Yun Feng Li、Cong Bin Ji、Shi Zhi Jiang、Wan Yi Liu

  DOI：10.1016/j.cclet.2010.04.038

  日期：2010.10

  A facile approach for the first synthesis of ocimarin, naturally occurring coumarins, was developed by employing a cerium (III) chloride heptahydrate-catalyzed Pechmann condensation of phenols and beta-keto esters in a solvent-free system as key step, by which ocimarin was achieved by three steps starting from acetylacetic ether and resorcinol with total yield 23.2%. All structures of new compounds were confirmed by IR, (1)H NMR and MS. (C) 2010 Jin Hui Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• ZAWADZKA, J.;SZCZYCINSKI, B.;FILCZEWSKI, M.;OLEDZKA, K., ACTA POL. PHARM., 1984, 41, N 6, 641-644
  作者：ZAWADZKA, J.、SZCZYCINSKI, B.、FILCZEWSKI, M.、OLEDZKA, K.

  DOI：——

  日期：——
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.