2-(9-氧代氧杂蒽-4-基)乙酸 | 35614-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-(9-氧代氧杂蒽-4-基)乙酸
• 英文名称: (9-oxo-9H-xanthen-4-yl)acetic acid
• 英文别名: 9-oxo-9H-xanthene-4-acetic acid；4-carboxymethyl-9-xanthenone；(xanthon-4-yl)acetic acid；xanthenone-4-acetic acid；xaa；9H-Xanthene-4-acetic acid, 9-oxo-；2-(9-oxoxanthen-4-yl)acetic acid
• CAS: 35614-21-2
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: ABGYSGBNWQSGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(9-氧代氧杂蒽-4-基)乙酸 在 phosphate buffer 作用下， 以 水 为溶剂， 生成 4-methylxanthen-9-one
  参考文献：
  名称：

  x吨酮乙酸的光脱羧：单峰激发态的CC键杂合。

  摘要：

  [反应：见正文]在含水缓冲液（pH 7.4）中辐照2-和4-蒽酮乙酸可导致有效的脱羧作用（分别为Phi = 0.67和0.64），得到相应的甲基产物，与中间的苄基碳负离子相符。荧光和激光闪光光解（LFP）研究表明，单重态反应性对于芳香族酮是不常见的。3-X吨酮乙酸在相同条件下是光惰性的。结果表明，反应性x吨酮乙酸是碳负离子介导的光笼的前体。

  DOI：

  10.1021/ol052953d
• 作为产物：
  描述：

  4-(bromomethyl)-9H-xanthen-9-one 在 硫酸 、 水 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(9-氧代氧杂蒽-4-基)乙酸
  参考文献：
  名称：

  Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo

  摘要：

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.

  DOI：

  10.1021/jm00124a012

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• Potential antitumor agents. 62. Structure-activity relationships for tricyclic compounds related to the colon tumor active drug 9-oxo-9H-xanthene-4-acetic acid
  作者：Gordon W. Rewcastle、Graham J. Atwell、Brian D. Palmer、Peter D. W. Boyd、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00106a003

  日期：1991.2

  molecular dipole moment lay out of the plane of the aromatic part of these molecules was found to be determined largely by the contributions from the acetic acid moiety relative to that from the tricyclic ring system. There did not appear to be any general relationship between the magnitude of the dipole moment and activity. However, for compounds containing the 9-carbonyl functionality, the orientation

  已经制备了一系列9-氧代-9H-氧杂蒽-4-乙酸的三环类似物，并评估了它们在小鼠皮下植入的结肠38肿瘤中引起出血性坏死的能力，以期扩展其结构-活性关系。这个系列。如先前在黄酮8-乙酸（FAA）的类似物中所发现的（Atwell等人，Anti-Cancer Drug Des。1989，4，161），XAA核的所有电子修饰均导致活性的严重降低或完全取消。 ，表明结构-活性关系狭窄。计算了许多化合物的偶极矩，发现分子偶极矩离开这些分子芳族部分平面的程度很大程度上取决于乙酸部分相对于乙酸部分的贡献。三环系统。偶极矩的大小与活动之间似乎没有任何一般的关系。但是，对于含有9-羰基官能团的化合物，偶极向量的方向可能很重要。在所有具有位于乙酸侧链周围的醚基的化合物中，该化合物与侧链OH之间存在接近的途径（约2.4 A）。
• Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation
  申请人：——

  公开号：US20040214798A1

  公开（公告）日：2004-10-28

  The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

  本发明涉及硝基芳基取代的磷酰胺前药化合物及其制备方法，用于靶向和抑制不良细胞生长或增殖。
• Photodecarboxylation of Xanthone Acetic Acids:  C−C Bond Heterolysis from the Singlet Excited State
  作者：Jessie A. Blake、Eric Gagnon、Matthew Lukeman、J. C. Scaiano

  DOI：10.1021/ol052953d

  日期：2006.3.1

  products, consistent with an intermediate benzylic carbanion. Fluorescence and laser flash photolysis (LFP) studies suggest singlet state reactivity, which is unusual for aromatic ketones. 3-Xanthone acetic acid is photoinert under the same conditions. The results suggest that the reactive xanthone acetic acids are promising precursors for carbanion-mediated photocages.

  [反应：见正文]在含水缓冲液（pH 7.4）中辐照2-和4-蒽酮乙酸可导致有效的脱羧作用（分别为Phi = 0.67和0.64），得到相应的甲基产物，与中间的苄基碳负离子相符。荧光和激光闪光光解（LFP）研究表明，单重态反应性对于芳香族酮是不常见的。3-X吨酮乙酸在相同条件下是光惰性的。结果表明，反应性x吨酮乙酸是碳负离子介导的光笼的前体。
• [EN] XANTHONE DERIVATIVES, UV PROTECTIVE COMPOSITION CONCENTRATE, METHOD OF PREPARATION OF UV PROTECTIVE COMPOSITION CONCENTRATE, USE OF UV PROTECTIVE COMPOSITION CONCENTRATE AND COSMETIC UV PROTECTIVE PRODUCT<br/>[FR] DÉRIVÉS DE XANTHONE, CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, PROCÉDÉ DE PRÉPARATION DE CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV, UTILISATION D'UN CONCENTRÉ DE COMPOSITION DE PROTECTION CONTRE LES UV ET PRODUIT COSMÉTIQUE DE PROTECTION CONTRE LES UV
  申请人：UNIV JAGIELLONSKI

  公开号：WO2021215943A1

  公开（公告）日：2021-10-28

  The first object of the invention is a xanthone derivative described by formula (I) where R1 is a substituent selected from the group comprising: hydrogen or alkoxy group; R2 is a substituent selected from the group comprising methylcinnamoyl, phenylpenta-2,4- dienenitrile, cyanoethenylphenyl or cyanoethenylalkyl substituent, wherein the phenyl ring is substituted with R3 selected from the group consisting of: hydrogen, alkoxy substituent or halide atom. The second objection of the invention is a UV protective composition concentrate containing the xanthone derivative described by the formula (I). The third object of the invention is a method for the preparation of a UV protective composition concentrate. The next object of the invention is the use of a UV protective composition concentrate for the production of UV protective cosmetic products. Yet another object of the invention is a cosmetic UV protective product.

  该发明的第一个对象是一种黄酮衍生物，其化学式为（I），其中R1是从包括：氢或烷氧基的基团中选择的取代基；R2是从包括：甲基肉桂酰基、苯基戊-2,4-二烯腈基、氰基乙烯基苯基或氰基乙烯基取代基中选择的取代基，其中苯环与R3选择自包括：氢、烷氧基取代基或卤素原子的基团。该发明的第二个对象是一种含有上述化学式（I）所述黄酮衍生物的紫外线防护组合物浓缩物。该发明的第三个对象是一种制备紫外线防护组合物浓缩物的方法。该发明的下一个对象是利用紫外线防护组合物浓缩物生产紫外线防护化妆品产品。该发明的另一个对象是一种化妆用紫外线防护产品。