3,4,6-trihydroxy-2-methoxy-5H-benzo[7]annulen-5-one | 4030-35-7

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 3,4,6-trihydroxy-2-methoxy-5H-benzo[7]annulen-5-one
• 英文别名: Purpurogallin-monomethylether；3,4,6-Trihydroxy-2-methoxybenzo[7]annulen-5-one；3,4,6-trihydroxy-2-methoxybenzo[7]annulen-5-one
• CAS: 4030-35-7
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: AVXUFKREYSJNGT-UHFFFAOYSA-N

物化性质

• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,6-trihydroxy-2-methoxy-5H-benzo[7]annulen-5-one 在 sodium hydroxide 、 双氧水 作用下， 生成 1',2',4'-Trihydroxy-3'-methoxy-3,4-benzotropolon
  参考文献：
  名称：

  1'，2'-二羟基-3,4-苯并呋喃酮的碱性过氧化物氧化

  摘要：

  1'，2'-二羟基-3,4-苯并呋喃酮的碱性过氧化物氧化反应通过相应的1'，2'-醌阴离子进行，该阴离子经历两种类型的过氧化物分解。（a）在低温和碱浓度下，过氧化物主要侵害环己二烯环的3'-和4'-位，并导致形成不稳定的氢过氧化物，其分解为羟基醌，这也直接通过溶剂分解而形成。3'-位的更高反应性归因于其与醌型和托酚酮羰基的共轭。由3'-取代的底物形成的2'-羟基-1'，4'-醌被进一步氧化为托酚酮-3,4-二羧酸酐。（b）在高温和碱浓度下会形成粘康酸通过过氧化氢引起的四羟基苯并呋喃酮和二羟基-2'，6'-醌类酮类化合物对tro环酮环的5位，6位和7位进行攻击。当底物在6-位带有羧基时，不会形成这些四羟基苯甲酮（也可通过水解1'，2'-醌的异常Thiele五乙酸酯获得）；在这种情况下，过氧化物对环己二烯环的1'-和2'-位的侵蚀占主导地位。

  DOI：

  10.1039/j39690000612
• 作为产物：
  描述：

  3-甲氧基儿茶酚 在 乙醚 、 3-tetrabromo-benzoquinone-(1.2) 作用下， 生成 3,4,6-trihydroxy-2-methoxy-5H-benzo[7]annulen-5-one
  参考文献：
  名称：

  Horner; Duerckheimer, Zeitschrift fur Naturforschung, 1959, vol. 14b, p. 741

  摘要：

  DOI：

文献信息

• Discovery of Small-Molecule Inhibitors of the TLR1/TLR2 Complex
  作者：Kui Cheng、Xiaohui Wang、Shuting Zhang、Hang Yin

  DOI：10.1002/anie.201204910

  日期：2012.12.3

  An important regulator of innate immunity, the protein complex of Toll‐like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU‐CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF‐α and IL‐1β

  作为先天免疫的重要调节剂， Toll 样受体 1 和 2 (TLR1/TLR2) 的蛋白质复合物为治疗各种免疫疾病提供了一个有吸引力的靶点。新型化合物 CU-CPT22 可以与特异性脂蛋白配体竞争结合 TLR1/TLR2（见图），具有高抑制活性和特异性。还观察到来自 TNF-α 和 IL-1β 的下游信号受到抑制。
• [EN] ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX<br/>[FR] ANTAGONISTES DU COMPLEXE DE RÉCEPTEUR 1/2 DE TYPE TOLL
  申请人：UNIV COLORADO REGENTS

  公开号：WO2014022287A1

  公开（公告）日：2014-02-06

  Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll¬ like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.

  提供了用于治疗Toll样受体1/2复合物（TLR1/2）相关炎症性疾病的化合物、组合物和方法。基于苯并三酮骨架的小分子，能够影响下游信号传导，以及制备和修改这些分子的方法也已披露。还提供了用于治疗与Toll样受体复合物1/2激活相关的临床状况的方法，包括向受试者施用有效量的苯并三酮化合物。
• STUDIES IN THE POLYOXYPHENOL SERIES: VI. THE OXIDATION OF PYROGALLOL AND VANILLIN BY ALKALINE HYPOIODITE AND HYPOCHLORITE
  作者：G. Denis Thorn、C. B. Purves

  DOI：10.1139/v54-050

  日期：1954.4.1

  Approximately 0.003 M solutions of pyrogallol and of vanillin in boric acid – sodium hydroxide buffers were used at 25 °C. to reduce hypoiodite and hypochlorite solutions made from sixfold molar amounts of the halogens. In all four cases the reduction reached a maximum in a narrow range near pH 9, and with hypoiodite the production of iodoform was restricted to this range. Slower secondary reductions were superimposed on very fast primary reactions. When oxidized with an equimolar amount of halogen near pH 8.5, vanillin gave a 90% yield of 5-iodovanillin and 65% of the 5-chloro derivative. These yields decreased with increasing alkalinity as the halogenations became slower. A new, simple preparation of trichloropyrogallol in 72% yield consisted of carrying out the chlorination with 3 moles of hypochlorite at pH 12. An equilibrium between pyrogallol–hypoiodite and 3-hydroxy-1,2-benzoquinone–iodide appeared to exist at the same pH.

  在25°C下，使用约0.003 M的丁香酚和香草醛在硼酸-氢氧化钠缓冲液中，用六倍摩尔量的卤素制备的次碘酸盐和次氯酸盐溶液进行还原。在所有四种情况下，还原在接近pH 9的狭窄范围内达到最大值，并且使用次碘酸盐时，碘仿的产量仅限于此范围。较慢的次要还原反应叠加在非常快速的主要反应上。在接近pH 8.5的条件下，与等摩尔量的卤素氧化，香草醛产生90%的5-碘香草醛收率和65%的5-氯衍生物收率。随着碱度的增加，这些收率降低，因为卤代反应变慢。72%收率的三氯丁香酚的新的简单制备方法包括在pH 12下用3摩尔次氯酸盐进行氯化。在相同的pH下，丁香酚-次碘酸盐和3-羟基-1,2-苯醌-碘化物之间似乎存在平衡。
• SOME METHYL ETHERS AND ACETATES OF PURPUROGALLIN
  作者：G. Denis Thorn、L. R. C. Barclay

  DOI：10.1139/v52-036

  日期：1952.4.1

  The preparation and ultraviolet absorption spectra of a number of methyl ethers and acetates of purpurogallin are given. The following derivatives of purpurogallin are, to our knowledge, not mentioned in the literature: a mono-acetate, m.p. 182-183 °C.; a diacetate I, m.p. 159–160 °C; a diacetate II, m.p. 208–209 °C.; a triacetate, m.p. 161.5–162.5 °C.; a monomethyl ether diacetate, m.p. 156–157 °C.; a dimethyl ether diacetate, m.p. 194-196 °C. Comparison of the ultraviolet absorption spectra with those determined for derivatives of known structure suggested the positions of the acetyl groups in the new substances now prepared.

  给出了一些紫胶单甲醚和醋酸甲酯的制备和紫外吸收光谱。以下紫胶衍生物据我们所知，在文献中没有提到：单醋酸酯，熔点182-183℃；二醋酸酯I，熔点159-160℃；二醋酸酯II，熔点208-209℃；三醋酸酯，熔点161.5-162.5℃；单甲醚二醋酸酯，熔点156-157℃；双甲醚二醋酸酯，熔点194-196℃。将紫外吸收光谱与已知结构衍生物的光谱进行比较，可以推断出新物质中乙酰基的位置。
• ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, a body corporate

  公开号：US20150251987A1

  公开（公告）日：2015-09-10

  Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are disclosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll-like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.

  提供了用于治疗Toll样受体1/2复合物（TLRI/2）相关炎症性疾病的化合物、组合物和方法。公开了基于苯并三环酮支架的小分子，能够影响下游信号传导，以及制备和修改这些分子的方法。还提供了用于治疗与Toll样受体复合物1/2激活相关的临床状况的方法，包括向受试者施用有效量的苯并三环酮化合物。