3-(bromomethyl)-9H-9-xanthenone | 118537-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(bromomethyl)-9H-9-xanthenone
• 英文别名: 3-bromomethyl-9H-xanthen-9-one；3-(bromomethyl)xanthen-9-one
• CAS: 118537-81-8
• 化学式: C₁₄H₉BrO₂
• 分子量: 289.128
• InChiKey: UXEWMLNEMMKNFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-9H-9-xanthenone 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-[[methyl(3-phenylprop-2-enyl)amino]methyl]xanthen-9-one
  参考文献：
  名称：

  Allylamine Type Xanthone Antimycotics

  摘要：

  A number of xanthone derivatives bearing the basic chain of naftifine and butenafine antimycotics in 1, 2, 3, and 4 nuclear positions are described. The in vitro antifungal activity against representative strains of molds and yeasts is reported. Only butenafine xanthone analogues shaw significant activity against Cryptococcus neoformans, in particular the regioisomer 4d (1.5 mu g/ml).

  DOI：

  10.1002/(sici)1521-4184(199806)331:6<225::aid-ardp225>3.0.co;2-5
• 作为产物：
  描述：

  3-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以60%的产率得到3-(bromomethyl)-9H-9-xanthenone
  参考文献：
  名称：

  一类新的非甾体芳香酶抑制剂：色酮和黄酮衍生物的设计与合成以及对P450酶芳香酶和17α-羟化酶/ C17,20-裂合酶的抑制作用。

  摘要：

  芳香酶（P450arom）是治疗乳腺癌的药理学目标。在本文中，我们报告了该酶的一系列新型（二）苯并吡喃酮类抑制剂的设计，合成和体外生物学评估。新化合物的设计以先前针对一系列非甾体芳香酶抑制剂开发的CoMFA模型为指导。色酮和黄嘌呤核均被视为分子骨架，其功能对于结合芳香酶活性位点至关重要-通过亚甲基与芳香部分相连的杂环（咪唑或1,3,4-三唑）单元和一个H键接受功能（CN，NO（2），Br）位于芳环上，与带有孤对的杂环氮相距合适的距离-并与它们相连。色酮，蒽酮，黄酮衍生物和黄酮衍生物通过常规合成方法由适当的甲基类似物制备。使用人胎盘微粒体和[1β，2β-（3）H]睾丸激素作为标记底物，通过Thompson和Siiteri的方法确定芳香酶抑制活性。还对所有化合物进行了17α-羟化酶/ C17,20-裂合酶（P450 17）的测试，这是一种治疗前列腺疾病的具有治疗意义的酶。x吨酮衍生物22d，e（IC（50）值分别为43和40

  DOI：

  10.1021/jm000955s

文献信息

• Quinuclidine derivative having tricyclic hetero condensed ring
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US05830902A1

  公开（公告）日：1998-11-03

  A quinuclidine derivative represented by the following general formula (I), a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, which has strong squalene synthase inhibiting activity and is useful as a cholesterol lowering agent without causing side effects. ##STR1## (Symbols in the formula represent the following meanings; R.sub.1 : a hydrogen atom, a halogen atom or a lower alkyl group, R.sub.2 : a hydrogen atom, a hydroxyl group or a lower alkoxy group, . . : a single bond or a double bond, with the proviso that R.sub.2 does not exist when . . . is a double bond, X and Y: the same or different from each other and each represents a bond, an oxygen atom (--O--), a carbonyl group (--CO--), a group represented by the formula --S(O).sub.p -- or a group represented by the formula --NR.sub.3 --, p: 0, 1 or 2, R.sub.3 : a hydrogen atom or a lower alkyl group which may have a substituent, A: a saturated or unsaturated lower alkylene group, a group of the formula --(CH.sub.2).sub.m Z(CH.sub.2).sub.n -- or a group of the formula --(CH.sub.2).sub.m Z(CH.sub.2).sub.n CR.sub.4 =, Z: an oxygen atom (--O--), a group of the formula --S(O).sub.q --, a carbonyl group (--CO--) or a group of the formula --NR.sub.5 --, R.sub.4 : a hydrogen atom, a halogen atom or a lower alkyl group, R.sub.5 : a hydrogen atom or a lower alkyl group, m and n: the same or different from each other and each is 0 or an integer of 1 to 5, m+n: an integer of 1 to 5 q: 0, 1 or 2, with the proviso that, when either one of X and Y is a bond, A is a group represented by the formula --(CH.sub.2).sub.m Z(CH.sub.2).sub.n CR.sub.4 =.)

  一种以以下一般式（I）表示的喹诺啉衍生物，其药学上可接受的盐、水合物或溶剂化合物，具有强烈的角鲨烯合酶抑制活性，可用作降低胆固醇的药物，而不会引起副作用。##STR1##（式中的符号表示以下含义；R.sub.1：氢原子、卤原子或较低的烷基基团，R.sub.2：氢原子、羟基或较低的烷氧基团，...：单键或双键，条件是当...为双键时，R.sub.2不存在，X和Y：相同或不同，每个代表键，氧原子（--O--），羰基（--CO--），由式--S(O).sub.p --表示的基团或由式--NR.sub.3 --表示的基团，p：0、1或2，R.sub.3：氢原子或可能具有取代基的较低烷基基团，A：饱和或不饱和的较低烷基基团，式--(CH.sub.2).sub.m Z(CH.sub.2).sub.n --的基团或式--(CH.sub.2).sub.m Z(CH.sub.2).sub.n CR.sub.4 =的基团，Z：氧原子（--O--），式--S(O).sub.q --的基团，羰基（--CO--）或式--NR.sub.5 --的基团，R.sub.4：氢原子、卤原子或较低烷基基团，R.sub.5：氢原子或较低烷基基团，m和n：相同或不同，每个为0或1至5的整数，m+n：1至5的整数，q：0、1或2，条件是当X和Y中的任一个为键时，A为由式--(CH.sub.2).sub.m Z(CH.sub.2).sub.n CR.sub.4 =表示的基团。
• Novel Highly Potent and Selective Nonsteroidal Aromatase Inhibitors: Synthesis, Biological Evaluation and Structure−Activity Relationships Investigation
  作者：Silvia Gobbi、Christina Zimmer、Federica Belluti、Angela Rampa、Rolf W. Hartmann、Maurizio Recanatini、Alessandra Bisi

  DOI：10.1021/jm100319h

  日期：2010.7.22

  In further pursuing our search for potent and selective aromatase inhibitors, a new series of molecules was designed and synthesized, exploring possible structural modifications of a previously identified xanthone scaffold. Among them, highly potent compounds, with inhibitory activity in the low nanomolar range, were found. In particular, substitution of the heterocyclic oxygen atom in the xanthone

  在进一步寻求有效和选择性芳香化酶抑制剂的过程中，设计并合成了一系列新分子，探索了先前鉴定的x吨酮骨架的可能结构修饰。其中，发现了在低纳摩尔范围内具有抑制活性的高效化合物。特别地，the吨酮核中的杂环氧原子被硫原子取代和/或结构柔性的增加似乎对于与酶的相互作用是有利的。
• 一类氧杂蒽酮类荧光染料及应用
  申请人：成都必凯科技有限公司

  公开号：CN108864058A

  公开（公告）日：2018-11-23

  本发明提供了一类氧杂蒽酮荧光染料及其在荧光探针的设计合成当中的应用，其具有如下结构通式I、II、III、IV：其中R1、R2、R3、R4分别选自氢、卤素、羟基、NH2、巯基、氰基、硝基、N，N‑双C1‑4烷基氨基、醛基、羧基、酰胺基、磺酰胺基、C5‑10芳基、C2‑8杂环芳基、C1‑6烷基、硼酸、硼酸频哪醇酯、OR(其中R为C1‑4的饱和烷基和不饱和烷基)。
• NOVEL QUINUCLIDINE DERIVATIVES HAVING TRICYCLIC FUSED HETERO RING
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0812840A1

  公开（公告）日：1997-12-17

  A quinuclidine derivative represented by the following general formula (I), a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, which has strong squalene synthase inhibiting activity and is useful as a cholesterol lowering agent without causing side effects. (Symbols in the formula represent the following meanings; R1: a hydrogen atom, a halogen atom or a lower alkyl group, R2: a hydrogen atom, a hydroxyl group or a lower alkoxy group, : a single bond or a double bond, with the proviso that R2 does not exist when is a double bond, X and Y: the same or different from each other and each represents a bond, an oxygen atom (-O-), a carbonyl group (-CO-), a group represented by the formula -S(O)p- or a group represented by the formula -NR3-, p: 0, 1 or 2, R3: a hydrogen atom or a lower alkyl group which may have a substituent, A: a saturated or unsaturated lower alkylene group, a group of the formula -(CH2)mZ(CH2)n- or a group of the formula -(CH2)mZ(CH2)nCR4=, Z: an oxygen atom (-O-), a group of the formula -S(O)q-, a carbonyl group (-CO-) or a group of the formula -NR5-, R4: a hydrogen atom, a halogen atom or a lower alkyl group, R5: a hydrogen atom or a lower alkyl group, m and n: the same or different from each other and each is 0 or an integer of 1 to 5, m + n: an integer of 1 to 5 q: 0, 1 or 2, with the proviso that, when either one of X and Y is a bond, A is a group represented by the formula -(CH2)mZ(CH2)nCR4=.)

  一种由以下通式（I）代表的喹烯酮衍生物、其药学上可接受的盐、其水合物或其溶液，该衍生物具有很强的角鲨烯合成酶抑制活性，可用作降低胆固醇的药物，且不会产生副作用。 (式中符号代表以下含义； R1：氢原子、卤素原子或低级烷基、 R2：氢原子、羟基或低级烷氧基、 R2：单键或双键，但 R2 为双键时不存在、 X和Y：彼此相同或不同，各自代表一个键、一个氧原子（-O-）、一个羰基（-CO-）、一个由式-S(O)p-代表的基团或一个由式-NR3-代表的基团、 p:0、1 或 2、 R3：氢原子或可带有取代基的低级烷基、 A：饱和或不饱和低级亚烷基、式-(CH2)mZ( )n-或式-( )mZ( )nCR4=的基团、 Z：氧原子（-O-）、式-S(O)q-的基团、羰基（-CO-）或式-NR5-的基团、 R4：氢原子、卤素原子或低级烷基、 R5：氢原子或低级烷基、 m 和 n：相同或互不相同，各自为 0 或 1 至 5 的整数、 m+n：1 至 5 的整数 q：0、1 或 2、 但条件是，当 X 和 Y 中任何一个是键时，A 是由式-( )mZ( )nCR4=代表的基团。）
• Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Stephen B. Calveley、William A. Denny

  DOI：10.1021/jm00124a012

  日期：1989.4

  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.