2-[(4-氟苯基)磺酰基]苯甲醛 | 1004293-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(4-氟苯基)磺酰基]苯甲醛
• 英文名称: 2-(4-fluorophenylsulfonyl)benzaldehyde
• 英文别名: 2-(4-Fluorobenzenesulfonyl)benzaldehyde；2-(4-fluorophenyl)sulfonylbenzaldehyde
• CAS: 1004293-27-9
• 化学式: C₁₃H₉FO₃S
• 分子量: 264.277
• InChiKey: AZCLVUSMWMZIQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(4-氟苯基)磺酰基]苯甲醛 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 水 、 氢碘酸 、 次磷酸 、 乙酸酐 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2-(dimethylamino)ethyl (3-{2-[(4-fluorophenyl)sulfonyl]benzyl}-2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-1yl)acetate
  参考文献：
  名称：

  New CRTH2 Antagonists

  摘要：

  本发明涉及一种式(I)的化合物，以及制备这种化合物的方法，以及它们在治疗通过CRTh2拮抗活性可改善的病理状况或疾病中的应用。

  公开号：

  EP2526945A1
• 作为产物：
  描述：

  1-(dimethoxymethyl)-2-(4-fluorophenylsulfonyl)benzene 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到2-[(4-氟苯基)磺酰基]苯甲醛
  参考文献：
  名称：

  WO2008/12511

  摘要：

  公开号：

文献信息

• [EN] INDOLIZINE DERIVATIVES WITH CRTH2 RECEPTOR AFFINITY FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS D'INDOLIZINE AVEC UNE AFFINITÉ POUR LE RÉCEPTEUR CRTH2 DESTINÉS AU TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：ARGENTA DISCOVERY LTD

  公开号：WO2009044147A1

  公开（公告）日：2009-04-09

  Compounds of formula (I) are ligands of the CRTH2 receptor, useful in the treatment of, for example, inflammatory respiratory disease: R1 is fluoro, chloro, CN or CF3; R2 is hydrogen, fluoro or chloro; X is -CH2-, or - S(O)n-; Ar1 is phenyl or 5- or 6-membered heteroaryl, wherein the phenyl or heteroaryl rings are optionally substituted with one substituent selected from fluoro, chloro, CN, -O(C1-C3alkyi) or C1-C3alkyl, the latter two groups being optionally substituted by one or more fluoro atoms; Y is -CR3R4-, -C(O)-, -O-, -S(O)2- or -NR3-; R3 and R4 independently represent hydrogen or C1-C3alkyl; Ar2 is phenyl or 5- or 6- membered heteroaryl, wherein the phenyl or heteroaryl rings are optionally substituted by one or more substituents independently selected from halogen, - CN, -S(O)nR5, -S(O)2NR6R7, -NR6S(O)2R5 -NR6R7, -NR6COR5, -CONR6R7, -COR5, -OR6, C1- C6alkyl or C3-C7cycloalkyl, the latter two groups being optionally substituted by one or more fluoro atoms; R5 is C1-C6alkyl or C3-C7cycloalkyl, optionally substituted by one or more fluoro atoms; R6 and R7 independently represent hydrogen, C1-C6alkyl or C3-C7cycloalkyl, the latter two groups being optionally substituted by one or more fluoro atoms; and n is O, 1 or 2.

  化合物的结构式（I）是CRTH2受体的配体，在治疗例如炎症性呼吸道疾病方面很有用：R1是氟、氯、CN或CF3；R2是氢、氟或氯；X是-CH2-或-S(O)n-；Ar1是苯基或5-或6-成员杂环基，其中苯基或杂环基环可以选择性地用来自氟、氯、CN、-O（C1-C3烷基）或C1-C3烷基的一个取代基取代，后两个基可以选择性地用一个或多个氟原子取代；Y是-CR3R4-，-C(O)-，-O-，-S(O)2-或-NR3-；R3和R4独立地代表氢或C1-C3烷基；Ar2是苯基或5-或6-成员杂环基，其中苯基或杂环基环可以选择性地用一个或多个取代基独立地选自卤素、-CN、-S(O)nR5、-S(O)2NR6R7、-NR6S(O)2R5、-NR6R7、-NR6COR5、-CONR6R7、-COR5、-OR6、C1-C6烷基或C3-C7环烷基取代，后两个基可以选择性地用一个或多个氟原子取代；R5是C1-C6烷基或C3-C7环烷基，可以选择性地用一个或多个氟原子取代；R6和R7独立地代表氢、C1-C6烷基或C3-C7环烷基，后两个基可以选择性地用一个或多个氟原子取代；n是O、1或2。
• Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists
  作者：Maria Antonia Buil、Marta Calbet、Marcos Castillo、Jordi Castro、Cristina Esteve、Manel Ferrer、Pilar Forns、Jacob González、Sara López、Richard S. Roberts、Sara Sevilla、Bernat Vidal、Laura Vidal、Pere Vilaseca

  DOI：10.1016/j.ejmech.2016.02.023

  日期：2016.5

  Monocyclic and bicyclic ring systems were investigated as the “core” section of a series of diphenylsulphone-containing acetic acid CRTh2 receptor antagonists. A range of potencies were observed and single-digit nanomolar potencies were obtained in both the monocyclic and bicyclic cores. Residence times for the monocyclic compounds were very short. Some of the bicyclic cores displayed better residence

  研究了单环和双环系统，将其作为一系列含二苯砜的乙酸CRTh2受体拮抗剂的“核心”部分。在单环和双环核中均观察到一定范围的效力，并获得了单位数纳摩尔的效力。单环化合物的停留时间非常短。一些双环核显示出更好的停留时间。在核心的北部，头部和尾部之间的甲基是开始长停留时间的必要条件。尾部取代的变化最大限度地提高了效力和停留时间。
• [EN] INDOLES AND THEIR THERAPEUTIC USE<br/>[FR] INDOLES ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：ARGENTA DISCOVERY LTD

  公开号：WO2009077728A1

  公开（公告）日：2009-06-25

  Compound of formula (I) are are ligands of the CRTH2 receptor, useful inter alia for treatment of inflammatory conditions. Wherein X is -SO2- or *-SO2NR3- wherein the bond marked with an asterisk is attached to Ar1; R1 is hydrogen, fluoro, chloro, CN or CF3; R2 is hydrogen, fluoro or chloro; R3 is hydrogen, C1C8alkyl or C3-C7cycloalkyl; Ar1 is phenyl or a 5- or 6-membered heteroaryl group selected from furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms; and Ar2 is phenyl or 5- or 6-membered heteroaryl group selected from pyrrolyl, furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl, wherein the phenyl or heteroaryl groups are optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3- C3- C7cycloalkyl, -O(C1-C4alkyl) or C1C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms.

  式(I)的化合物是CRTH2受体的配体，尤其适用于治疗炎症性疾病。其中，X为-SO2-或*-SO2NR3-，其中带有星号的键连接到Ar1；R1为氢、氟、氯、氰基或三氟甲基；R2为氢、氟或氯；R3为氢、C1-C8烷基或C3-C7环烷基；Ar1为苯基或选自呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代；Ar2为苯基或选自吡咯基、呋喃基、噻吩基、噁唑基、噻唑基、咪唑基、吡唑基、异噁唑基、异噻唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基的5或6元杂芳基，其中苯基或杂芳基可任选地被一个或多个独立选自氟、氯、氰基、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基的取代基取代，后两个基团可任选地被一个或多个氟原子取代。
• [EN] INDOLES ACTIVE ON CRTH2 RECEPTOR<br/>[FR] INDOLES ACTIFS SUR LE RÉCEPTEUR CRTH2
  申请人：ARGENTA DISCOVERY LTD

  公开号：WO2009090399A1

  公开（公告）日：2009-07-23

  Indole derivatives having therapeutic utility are of formula (I): X is -SO2- or *-SO2NR3- wherein the bond marked with an asterisk is attached to Ar1; R1 and R2 are, independently, hydrogen, fluoro, chloro, CN or CF3; R3 is hydrogen, C1-C8alkyl or C3-C7cycloalkyl; and Ar1 and Ar2 are, independently, phenyl or a 5- or 6-membered heteroaryl group, wherein the phenyl or heteroaryl group is optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C3-C7cycloalkyl, -O(C1-C4alkyl) or C1-C6alkyl, the latter two groups being optionally substituted by one or more fluoro atoms.

  具有治疗作用的吲哚衍生物的化学式为(I)：X为-SO2-或*-SO2NR3-，其中带有星号标记的键连接到Ar1；R1和R2独立地为氢、氟、氯、CN或CF3；R3为氢、C1-C8烷基或C3-C7环烷基；Ar1和Ar2独立地为苯基或5-或6-成员杂环基团，其中苯基或杂环基团可选择地被一个或多个取代基取代，这些取代基独立地由氟、氯、CN、C3-C7环烷基、-O(C1-C4烷基)或C1-C6烷基中的一个或多个选择，后两个基可选择地被一个或多个氟原子取代。
• Indoles Active on CRTH2 Receptor
  申请人：Hynd George

  公开号：US20110060026A1

  公开（公告）日：2011-03-10

  Indole derivatives having therapeutic utility are of formula (I): X is —SO 2 — or *—SO 2 NR 3 — wherein the bond marked with an asterisk is attached to Ar 1 ; R 1 and R 2 are, independently, hydrogen, fluoro, chloro, CN or CF 3 ; R 3 is hydrogen, C 1 -C 8 alkyl or C 3 -C 7 cycloalkyl; and Ar 1 and Ar 2 are, independently, phenyl or a 5- or 6-membered heteroaryl group, wherein the phenyl or heteroaryl group is optionally substituted by one or more substituents independently selected from fluoro, chloro, CN, C 3 -C 7 cycloalkyl, —O(C 1 -C 4 alkyl) or C 1 -C 6 alkyl, the latter two groups being optionally substituted by one or more fluoro atoms.

  具有治疗效用的吲哚衍生物的化学式为(I)：其中X为—SO2—或*—SO2NR3—，其中带有星号标记的键连接到Ar1；R1和R2独立地为氢、氟、氯、CN或CF3；R3为氢、C1-C8烷基或C3-C7环烷基；Ar1和Ar2独立地为苯基或5-或6-成员杂环芳基基团，其中苯基或杂环芳基基团可选地被一个或多个取代基独立地选自氟、氯、CN、C3-C7环烷基、—O(C1-C4烷基)或C1-C6烷基，后两种基团可选地被一个或多个氟原子取代。