6-phenylpiperonylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-phenylpiperonylic acid
• 英文别名: 6-phenylbenzo[d][1,3]dioxole-5-carboxylic acid；6-Phenyl-piperonylsaeure；5-Phenyl-piperonylic acid；6-phenyl-1,3-benzodioxole-5-carboxylic acid
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: OOIPMQWPWABQSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-phenylpiperonylic acid 在 过氧乙酸 、 六氟异丙醇 、 4-碘甲苯 、 溶剂黄146 作用下， 反应 16.0h， 以60%的产率得到6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]chromen-6-one
  参考文献：
  名称：

  轻度ArI催化的C（sp2）？H或C（sp3）？H功能化/ C ？O的形成：一个有趣的催化剂控制的选择性开关

  摘要：

  C（SP A串联2） H和C（SP 3） ħ官能/ C 由碘催化O键形成原位产生（III）的试剂已经被开发出来。该方法在温和条件下显示范围广，并且显示出前所未有的选择性曲线，可以根据所用催化剂进行切换。

  DOI：

  10.1002/anie.201407011
• 作为产物：
  描述：

  胡椒酸 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 6-phenylpiperonylic acid
  参考文献：
  名称：

  通过光催化还原自由基自环化全合成 Zephycarinatines

  摘要：

  摘要我们在此报告了一种用于全合成 plicamine 型生物碱 zephycarinatines C 和 D 的非仿生策略。合成的关键特征是立体选择性还原自由基依索‐使用可见光介导的光氧化还原催化进行环化。这种环化通过在芳香环上添加碳中心基团，能够构建 6,6-螺环核心结构。对 zephycarinatines 及其衍生物的生物学评价表明，带有酮基的合成衍生物对 LPS 诱导的 NO 产生具有中等的抑制活性。这种方法可以为未来扩大 plicamine 型生物碱的化学多样性提供机会，并为其合成提供有用的中间体。

  DOI：

  10.1002/ange.202009399

文献信息

• Dihydropyridine-, pyridine-, benzopyranone- and triazoloquinazoline derivatives, their preparation and their use as adenosine receptor antagonists
  申请人：The United States of America, Represented by the Secretary, Department of Health and Human Services

  公开号：EP2311806A2

  公开（公告）日：2011-04-20

  The present invention provides certain novel compounds, compositions, and a method of treating a mammal by blocking its adenosine receptors comprising administering at least one compound of the present invention. Examples of the present inventive compounds include certain flavonoids of formulae (I) and (II), wherein R1 to R4 are as defined in the description, and M is -CH (OH) -CH (R2) - or -C(OH)=C(R2)- and R1, R2 are as defined in the description; or dihydropyridines of formula (III), wherein R2 to R6 are as defined in the description; or pyridines of formula (IV), wherein R2 to R6 are as defined in the description, or triazoloquinazolines of formula (V), wherein R1 and R2 are as defined in the description; and their derivatives, or pharmaceutically acceptable salts thereof.

  本发明提供了某些新型化合物、组合物以及一种通过阻断哺乳动物的腺苷受体来治疗哺乳动物的方法，该方法包括施用至少一种本发明化合物。本发明化合物的实例包括某些式(I)和(II)的黄酮类化合物，其中R1至R4如说明中所定义，M为-CH(OH)-CH(R2)-或-C(OH)＝C(R2)-且R1、R2如说明中所定义；或式(III)的二氢吡啶类化合物，其中R2至R6如说明中所定义；或式（IV）的吡啶，其中 R2 至 R6 如说明书中定义；或式（V）的三唑并喹唑啉，其中 R1 和 R2 如说明书中定义；以及它们的衍生物或药学上可接受的盐。
• Interactions of Flavonoids and Other Phytochemicals with Adenosine Receptors
  作者：Xiao-duo Ji、Neli Melman、Kenneth A. Jacobson

  DOI：10.1021/jm950661k

  日期：1996.1.1

  Flavone derivatives and other phytochemicals were found to bind to three subtypes of adenosine receptors in the micromolar range. Affinity was determined in radioligand binding assays at rat brain A(1) and A(2A) receptors using [H-3]-N-6-PIA ([H-3]-(R)-N-6-phenylisopropyladenosine) and [H-3]CGS21680 ([H-3]-2-[[4-(2-carboxyethyl)phenyl]ethyl respectively. Affinity was determined at cloned human and rat brain A(3) receptors using [I-125]-AB-MECA [N-6-(4-amino-3-iodobenzyl)adenosine-5'(N-methyluronamide)]. A structure-activity analysis indicated that the hydroxyl groups of naturally occurring flavones are not essential for affinity at adenosine receptors. Galangin, 14, displayed K-i values of 1 mu M at both rat A(1) and A(2A) receptors and 3 mu M at human A(3) receptors. Methylation but not acetylation of the hydroxyl groups of galangin enhanced A(3) affinity. Pentamethylmorin, 20, appeared to bind with 14-17-fold selectivity for human A(3) receptors vs rat A(1) and A(2A) receptors, with a K-i value of 2.65 mu M. Two flavone derivatives (14 and 15) showed 14-fold greater affinity at human vs rat A(3) receptors. Reduction of the 2,3-olefinic bond, as in (+/-)-dihydroquercetin, or glycosidation, as in robinin, greatly diminished affinity. An isoflavone, genistein, also bound only very weakly at 47 receptors. alpha-Naphthoflavone had greater receptor affinity (0.79 mu M at A(1) receptors) than the beta-isomer. Other natural products of plant origin, including oxogalanthine lactam, hematoxylin, and arborinine were found to bind to A(1) adenosine receptors with K-i values of 3-13 mu M. These findings indicate that the flavones, flavonols, flavanones, and other phytochemicals may provide leads for the development of novel adenosine antagonists. The unexpected finding of considerable affinity of flavones at both rat and human A(3) receptors may explain some of the previously observed biological effects of these compounds.
• DIHYDROPYRIDINE-, PYRIDINE-, BENZOPYRAN- ONE- AND TRIAZOLOQUINAZOLINE DERIVATIVE, THEIR PREPARATION AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS
  申请人：THE UNITED STATES OF AMERICA, as represented by the Secretary of the Department of Health and Human Services

  公开号：EP0885192A1

  公开（公告）日：1998-12-23
• US6066642A
  申请人：——

  公开号：US6066642A

  公开（公告）日：2000-05-23
• [EN] DIHYDROPYRIDINE-, PYRIDINE-, BENZOPYRAN- ONE- AND TRIAZOLOQUINAZOLINE DERIVATIVE, THEIR PREPARATION AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE DIHYDROPYRIDINE-, PYRIDINE-, BENZOPYRANE- MONO- ET TRIAZOLOQUINAZOLINE, LEUR PREPARATION, ET UTILSATION COMME ANTAGONISTES DES RECEPTEURS DE L'ADENOSINE
  申请人：——

  公开号：WO1997027177A2

  公开（公告）日：1997-07-31

  [EN] The present invention provides certain novel compounds, compositions, and a method of treating a mammal by blocking its adenosine receptors comprising administering at least one compound of the present invention. Examples of the present inventive compounds include certain flavonoids of formulae (I) and (II), wherein R1 to R4 are as defined in the description, and M is -CH(OH)-CH(R2) or -C(OH)=C(R2)- and R1, R2 are as defined in the description; or dihydropyridines of formula (III), wherein R2 to R6 are as defined in the description; or pyridines of formula (IV), wherein R2 to R6 are as defined in the description, or triazoloquinazolines of formula (V) wherein R1 and R2 are as defined in the description; and their derivatives, or pharmaceutically acceptable salts thereof.
  [FR] La présente invention concerne certains composés, compositions et thérapies pour le traitement d'un mammifère par blocage de ses récepteurs de l'adénosine. Cette thérapie consiste en l'administration d'au moins un composé de la présente invention. Les principaux composés de l'invention contiennent: certaines flavonoïdes représentées par les formules générales (I) et (II), où R1 à R4 sont conformes à leurs définition dans la description, M est -CH(OH)-(CH(R2)- ou C(OH)=C(R2)- et R1 et R2 sont conformes à leurs définitions dans la description; ou des dihydropyridines représentées par la formule générale (III) où R2 à R6 sont conformes à leurs définitions dans la description; ou des pyridines représentées par la formule générale (IV) où R2 à R6 sont conformes à leurs définitions dans la description; ou des triazoloquinazolines représentées par la formule générale (V) où R2 à R6 sont conformes à leurs définitions dans la description. L'invention concerne également leurs dérivés, ou certains de leurs sels galéniques.