3-<2-(dimethylamino)ethoxy>-4-nitroanisole | 170229-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<2-(dimethylamino)ethoxy>-4-nitroanisole
• 英文别名: [2-(2-methoxy-5-nitrophenoxy)ethyl]dimethylamine；2-(2-Dimethylaminoethoxy)-4-nitroanisole；2-(2-methoxy-5-nitrophenoxy)-N,N-dimethylethanamine
• CAS: 170229-67-1
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: JYEQXKGFYKEUOA-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±32.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<2-(dimethylamino)ethoxy>-4-nitroanisole 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-[3-[2-(二甲基氨基)乙氧基]-4-甲氧基苯基]-2'-甲基-4'-(5-甲基-1,2,4-恶二唑-3-基)-[1,1'-联苯]-4-甲酰胺
  参考文献：
  名称：

  The Selective 5-HT_1B Receptor Inverse Agonist 1‘-Methyl-5-[[2‘-methyl-4‘- (5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro- spiro[furo[2,3-f]indole-3,4‘-piperidine] (SB-224289) Potently Blocks Terminal 5-HT Autoreceptor Function Both in Vitro and in Vivo

  摘要：

  5-HT1 receptors are members of the G-protein-coupled receptor superfamily and are negatively Linked to adenylyl cyclase activity. The human 5-HT1B and 5-HT1D receptors (previously known as 5-HT1D beta and 5-HT1D alpha, respectively), although encoded by two distinct genes, are structurally very similar. Pharmacologically, these two receptors have been differentiated using nonselective chemical tools such as ketanserin and ritanserin, but the absence of truly selective agents has meant that the precise function of the 5-HT1B and 5-HT1D receptors has not been defined. In this paper we describe how, using computational chemistry models as a guide, the nonselective 5-HT1B/5-HT1D receptor antagonist 4 was structurally modified to produce the selective 5-HT1B receptor inverse agonist 5, 1'-methyl-5-[[2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (SB-224289). This compound is a potent antagonist of terminal 5-HT autoreceptor function both in vitro and in vivo.

  DOI：

  10.1021/jm970457s
• 作为产物：
  描述：

  2-甲氧基-5-硝基苯酚 、 二甲氨基氯乙烷盐酸 在 sodium hydride 、 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 5.0h， 以65%的产率得到3-<2-(dimethylamino)ethoxy>-4-nitroanisole
  参考文献：
  名称：

  WO2006/91963

  摘要：

  公开号：

文献信息

• HETEROCYCLIC COMPOUNDS
  申请人：GAUL Christoph

  公开号：US20090203688A1

  公开（公告）日：2009-08-13

  The invention relates to compounds of formula I and salts thereof wherein the substituents are as defined in the specification, processes for the preparation thereof; to pharmaceuticals containing such compounds, in particular for the use in one or more Protein tyrosine kinase mediated diseases.

  该发明涉及公式I的化合物及其盐，其中取代基如规范中定义，以及其制备方法；含有这种化合物的药物，特别用于在一个或多个蛋白酪氨酸激酶介导的疾病中使用。
• [EN] CYCLIC UREA DERIVATIVES WITH 5-HT2C RECEPTOR ACTIVITY<br/>[FR] DERIVES CYCLIQUES D'UREE POSSEDANT UNE ACTIVITE DE RECEPTEURS 5-HT2C
  申请人：GLAXO GROUP LTD

  公开号：WO2003057220A1

  公开（公告）日：2003-07-17

  Compounds of formula (I) or a pharmaceutically acceptable salt thereof, having 5HT2C receptor activity, are disclosed: wherein a is 0, 1, 2, 3, 4 or 5; b is 1, 2 or 3; Y is nitrogen or carbon; A is oxygen, nitrogen, -CONH-, -NHCO- or together with R2 form a benzoxazolone group; R1 is halogen, C¿1-6?alkyl, C1-6alkoxy, C1-6alkylthio, hydroxy, amino, mono- or di-C1-6alkylamino, nitro, CN, CF3, OCF3, aryl, arylC1-6alkyl, arylC1-6alkyloxy or arylC1-6alkylthio; R?2¿ is hydrogen, halogen, C¿1-6?alkyl, C1-6alkoxy, haloC1-6alkyl or haloC1-6alkoxy; R?3¿ is: (i) -NR4R5 where R?4 and R5¿ are independently hydrogen, C¿1-6?alkyl or arylC1-6alkyl; or (ii) an optionally substituted N-linked heterocycle; or (iii) an optionally substituted C-linked heterocycle; ======= is a single bond or a double bond; and X is CH2 or C = O (when ======= is a single bond) or X is CH (when ======= is a double bond). The preparation of these compounds and their use in therapy, especially for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式（I）的化合物或其药学上可接受的盐，具有5HT2C受体活性：其中a为0、1、2、3、4或5；b为1、2或3；Y为氮或碳；A为氧、氮、-CONH-、-NHCO-或与R2一起形成苯并噁唑酮基团；R1为卤素、C1-6烷基、C1-6烷氧基、C1-6烷基硫基、羟基、氨基、单基或双C1-6烷基氨基、硝基、CN、CF3、OCF3、芳基、芳基C1-6烷基、芳基C1-6烷氧基或芳基C1-6烷硫基；R2为氢、卤素、C1-6烷基、C1-6烷氧基、卤代C1-6烷基或卤代C1-6烷氧基；R3为：（i）-NR4R5，其中R4和R5独立地为氢、C1-6烷基或芳基C1-6烷基；或（ii）可选地取代的N-连接杂环；或（iii）可选地取代的C-连接杂环；=======为单键或双键；X为CH2或C = O（当=======为单键时）或X为CH（当=======为双键时）。还公开了这些化合物的制备及其在治疗中的用途，特别是用于中枢神经系统疾病，如抑郁症或焦虑症。
• Cyclic urea derivatives with 5-ht2c receptor activity
  申请人：Bromidge M Steven

  公开号：US20050154028A1

  公开（公告）日：2005-07-14

  Compounds of formula (I) or a pharmaceutically acceptable salt thereof, having 5HT 2C receptor activity, are disclosed: wherein a is 0,1,2,3,4 or 5; b is 1,2 or 3; Y is nitrogen or carbon; A is oxygen, nitrogen, —CONH—, —NHCO— or together with R 2 form a benzoxazolone group; R 1 is halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, hydroxy, amino, mono- or di-C 1-6 alkylamino, nitro, CN, CF 3 , OCF 3 , aryl, arylC 1-6 alkyl, arylC 1-6 alkyloxy or arylC 1-6 alkylthio; R 2 is hydrogen, halogen, C 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkyl or haloC 1-6 alkoxy; R 3 is: (i) —NR 4 R 5 where R 4 and R 5 are independently hydrogen, C 1-6 alkyl or arylC 1-6 alkyl; or (ii) an optionally substituted N-linked heterocycle; or (iii) an optionally substituted C-linked heterocycle; ======= is a single bond or a double bond; and X is CH 2 or C═O (when ======= is a single bond) or X is CH (when ======= is a double bond). The preparation of these compounds and their use in therapy, especially for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式(I)化合物或其药学上可接受的盐，具有5HT2C受体活性：其中a为0、1、2、3、4或5；b为1、2或3；Y为氮或碳；A为氧、氮、-CONH-、-NHCO-或与R2一起形成苯并噁唑酮基团；R1为卤素、C1-6烷基、C1-6烷氧基、C1-6烷基硫基、羟基、氨基、单-或双C1-6烷基氨基、硝基、CN、CF3、OCF3、芳基、芳基C1-6烷基、芳基C1-6烷氧基或芳基C1-6烷硫基；R2为氢、卤素、C1-6烷基、C1-6烷氧基、卤代C1-6烷基或卤代C1-6烷氧基；R3为：（i）-NR4R5，其中R4和R5独立地为氢、C1-6烷基或芳基C1-6烷基；或（ii）可选地取代的N-连接杂环；或（iii）可选地取代的C-连接杂环；=======为单键或双键；X为CH2或C═O（当=======为单键时）或X为CH（当=======为双键时）。还公开了这些化合物的制备及其在治疗中的使用，特别是用于中枢神经系统障碍，如抑郁症或焦虑症。
• Benzene, pyridine, and pyridazine derivatives
  申请人：Huang He Kenneth

  公开号：US20060211737A1

  公开（公告）日：2006-09-21

  Disclosed are compounds and pharmaceutically acceptable salts of Formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , n, Q 1 , Q 2 , Q 3 , Y, and X 1 -X 4 are as defined herein. Compounds of Formula I are useful in the treatment of diseases and/or conditions related to cell proliferation, such as cancer, inflammation, arthritis, angiogenesis, or the like. Also disclosed are pharmaceutical compositions comprising compounds of the invention and methods of treating the aforementioned conditions using such compounds.

  本发明涉及式I的化合物和药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、n、Q1、Q2、Q3、Y和X1-X4如本文所定义。式I的化合物在治疗与细胞增殖相关的疾病和/或病况方面有用，例如癌症、炎症、关节炎、血管生成或类似的疾病。本发明还涉及包括该化合物的药物组合物和使用这种化合物治疗上述疾病的方法。
• Heterocyclic biphenylylamides useful as 5HT1D antagonists
  申请人：SmithKline Beecham plc

  公开号：US05801170A1

  公开（公告）日：1998-09-01

  A compound of formula (I) or a salt thereof: ##STR1## wherein P is a 5 to 7 membered heterocyclic ring selected from the group consisting of thienyl, furyl, pyrrolyl, triazolyl, diazolyl, tetrazolyl, imidazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimdyl and pyrazinyl; R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, hydroxyC.sub.1-6 alkyl, C.sub.1-6 alkylOC.sub.1-6 alkyl, alkanoyl, optionally substituted phenyl, alkanoyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO.sub.2 R.sup.9,CONR.sup.10 R.sup.11 where R.sup.9, R.sup.10 and R.sup.11 are independently hydrogen or C.sub.1-6 alkyl; R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-6 alkyl; R.sup.6 is hydrogen, halogen, hydroxy, C.sub.1-6 alkyl or C.sub.1-6 alkoxy R.sup.7 and R.sup.8 are independently hydrogen, C.sub.1-6 alkyl, a optionally substituted phenylalkyl or together with the nitrogen atom to which they are attached form an optionally substituted 5- to 7-membered heterocyclic ring containing one or two heteroatoms selected from oxygen, nitrogen or sulphur; A is CONH or NHCO; B is oxygen, S(O)p where p is 0, 1 or 2, NR.sup.12 where R.sup.12 is hydrogen, C.sub.1-6 alkyl or phenylC.sub.1-6 alkyl, or B is CR.sup.4 .dbd.CR.sup.5 or CR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-6 alkyl; m is 1 to 4; and n is 1 or 2.

  化合物的式(I)或其盐：##STR1## 其中P是从噻吩基、呋喃基、吡咯基、三唑基、二唑基、四唑基、咪唑基、噁二唑基、异噻唑基、异恶唑基、噻二唑基、吡啶基、嘧啶基和吡嗪基中选择的5至7元杂环；R.sup.1、R.sup.2和R.sup.3独立地表示氢、卤素、C.sub.1-6烷基、C.sub.3-6环烷基、C.sub.3-6环烯基、C.sub.1-6烷氧基、羟基C.sub.1-6烷基、C.sub.1-6烷氧基C.sub.1-6烷基、酰基、可选取代的苯基、酰氧基、羟基、硝基、三氟甲基、氰基、CO.sub.2R.sup.9、CONR.sup.10R.sup.11，其中R.sup.9、R.sup.10和R.sup.11独立地表示氢或C.sub.1-6烷基；R.sup.4和R.sup.5独立地表示氢或C.sub.1-6烷基；R.sup.6表示氢、卤素、羟基、C.sub.1-6烷基或C.sub.1-6烷氧基；R.sup.7和R.sup.8独立地表示氢、C.sub.1-6烷基、可选取代的苯基烷基，或者与它们所连接的氮原子一起形成一个选自氧、氮或硫的一个或两个杂原子的可选取代的5至7元杂环；A是CONH或NHCO；B是氧、S(O)p，其中p为0、1或2，NR.sup.12，其中R.sup.12表示氢、C.sub.1-6烷基或苯基C.sub.1-6烷基，或者B是CR.sup.4.dbd.CR.sup.5或CR.sup.4R.sup.5，其中R.sup.4和R.sup.5独立地表示氢或C.sub.1-6烷基；m为1至4；n为1或2。