2-Amino-5,N,N-trimethyl-benzamide | 178672-23-6

• 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: 2-Amino-5,N,N-trimethyl-benzamide
• 英文别名: 2-amino-N,N,5-trimethylbenzamide
• CAS: 178672-23-6
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: ZJSZIIIESSNAIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Amino-5,N,N-trimethyl-benzamide 、 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl methanesulfonate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 25.0h， 以48%的产率得到2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-N,N,5-trimethylbenzamide
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j
• 作为产物：
  描述：

  N,N,5-trimethyl-2-nitrobenzamide 在 钯 氢气 、 silica gel 、 dichloromethane ethanol 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以to give 2-amino-N,N,5-trimethylbenzamide (8 g, 44.9 mmol), m.p. 98°-99° C.的产率得到2-Amino-5,N,N-trimethyl-benzamide
  参考文献：
  名称：

  \x9b3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine,

  摘要：

  本发明涉及一种新型的α1-肾上腺素受体拮抗剂，其化学式为I：##STR1## 其中：p为0或1；t为0、1或2；X为O、S或NR6（其中R6为氢或（C1-6）烷基）；Y和Z独立地为CH或N；R1为氢、羟基、卤素、硝基、氨基、氰基、（C1-4）烷基硫醇、乙酰氨基、三氟乙酰氨基、甲基磺酰氨基、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-4）烷基、噁唑-2-基、芳基、杂环芳基、芳基（C1-4）烷基、杂环芳基（C1-4）烷基、（C1-6）烷氧基、（C3-6）环烷氧基、（C3-6）环烷基（C1-4）烷氧基、2-丙炔氧基、芳基氧基、杂环芳基氧基、芳基（C1-4）烷氧基或杂环芳基（C1-4）烷氧基（其中烷基可选地被1-3个卤素原子取代，芳基或杂环芳基可选地被1-2个独立选择自卤素和氰基的取代基取代）；R2为氢、羟基、卤素、氰基、（C1-6）烷基或（C1-6）烷氧基（其中烷基可选地被1-3个卤素原子取代）；R3为-C（O）R7（其中R7为（C1-6）烷基、（C3-6）环烷基、二（C1-4）烷基氨基、N-（C1-4）烷基-N-（C1-4）烷氧基氨基、（C1-4）烷基（（C1-4）烷氧基）氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基）；R4为卤素、羟基、氰基、（C1-6）烷基或（C1-6）烷氧基；R5为（C1-6）烷基；以及其药学上可接受的盐和N-氧化物。

  公开号：

  US05688795A1

文献信息

• \x9b3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine,
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05688795A1

  公开（公告）日：1997-11-18

  The present invention relates to novel .alpha..sub.1 -adrenoceptor antagonists of Formula I: ##STR1## in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR.sup.6 (in which R.sup.6 is hydro or (C.sub.1-6)alkyl); Y and Z are independently CH or N; R.sup.1 is hydro, hydroxy, halo, nitro, amino, cyano, (C.sub.1-4)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C.sub.1-6)alkyl, (C.sub.3-6)cycloalkyl, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl (C.sub.1-4)alkyl, heteroaryl (C.sub.1-4)alkyl, (C.sub.1-6)alkyloxy, (C.sub.3-6)cycloalkyloxy, (C.sub.3-6)cycloalkyl (C.sub.1-4)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl (C.sub.1-4)alkyloxy or heteroaryl (C.sub.1-4)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R.sup.2 is hydro, hydroxy, halo, cyano, (C.sub.1-6)alkyl or (C.sub.1-6)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R.sup.3 is -C (O)R.sup.7 (wherein R.sup.7 is (C.sub.1-6)alkyl, (C.sub.3-6)cycloalkyl, di(C.sub.1-4)alkylamino, N-(C.sub.1-4)alkyl-N-(C.sub.1-4)alkyloxyamino, (C.sub.1-4)alkyl((C.sub.1-4)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R.sup.4 is halo, hydroxy, cyano, (C.sub.1-6)alkyl or (C.sub.1-6)alkyloxy; and R.sup.5 is (C.sub.1-6)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及一种新型的α1-肾上腺素受体拮抗剂，其化学式为I：##STR1## 其中：p为0或1；t为0、1或2；X为O、S或NR6（其中R6为氢或（C1-6）烷基）；Y和Z独立地为CH或N；R1为氢、羟基、卤素、硝基、氨基、氰基、（C1-4）烷基硫醇、乙酰氨基、三氟乙酰氨基、甲基磺酰氨基、（C1-6）烷基、（C3-6）环烷基、（C3-6）环烷基（C1-4）烷基、噁唑-2-基、芳基、杂环芳基、芳基（C1-4）烷基、杂环芳基（C1-4）烷基、（C1-6）烷氧基、（C3-6）环烷氧基、（C3-6）环烷基（C1-4）烷氧基、2-丙炔氧基、芳基氧基、杂环芳基氧基、芳基（C1-4）烷氧基或杂环芳基（C1-4）烷氧基（其中烷基可选地被1-3个卤素原子取代，芳基或杂环芳基可选地被1-2个独立选择自卤素和氰基的取代基取代）；R2为氢、羟基、卤素、氰基、（C1-6）烷基或（C1-6）烷氧基（其中烷基可选地被1-3个卤素原子取代）；R3为-C（O）R7（其中R7为（C1-6）烷基、（C3-6）环烷基、二（C1-4）烷基氨基、N-（C1-4）烷基-N-（C1-4）烷氧基氨基、（C1-4）烷基（（C1-4）烷氧基）氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基）；R4为卤素、羟基、氰基、（C1-6）烷基或（C1-6）烷氧基；R5为（C1-6）烷基；以及其药学上可接受的盐和N-氧化物。
• Selected Benzofuran Derivatives
  申请人：Greiveldinger-Poenaru Sorana

  公开号：US20080108610A1

  公开（公告）日：2008-05-08

  The invention relates to new benzofuran derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds, and especially their use as anti-infectives.

  本发明涉及新的苯并呋喃衍生物及其在制备药物组成物中作为活性成分的用途。本发明还涉及相关方面，包括制备该化合物的过程、含有其中一种或多种化合物的药物组成物，尤其是它们作为抗感染剂的用途。
• 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy -pyridine, pyrimidine and benzene derivatives as alpha1-adrenoceptor antagonists
  申请人：F. Hoffmann-La Roche AG

  公开号：EP0711757A1

  公开（公告）日：1996-05-15

  The present invention relates to novel α₁-adrenoceptor antagonists of Formula I: in which: p is 0 or 1; t is 0, 1 or 2; X is O, S or NR⁶ (in which R⁶ is hydro or (C₁₋₆)alkyl); Y and Z are independently CH or N; R¹ is hydro, hydroxy, halo, nitro, amino, cyano, (C₁₋₄)alkylthio, acetylamino, trifluoroacetylamino, methylsulfonylamino, (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, (C₃₋₆)cycloalkyl(C₁₋₄)alkyl, oxazol-2-yl, aryl, heteroaryl, aryl(C₁₋₄)alkyl, heteroaryl(C₁₋₄)alkyl, (C₁₋₆)alkyloxy, (C₃₋₆)cycloalkyloxy, (C₃₋₆)cycloalkyl(C₁₋₄)alkyloxy, 2-propynyloxy, aryloxy, heteroaryloxy, aryl(C₁₋₄)alkyloxy or heteroaryl(C₁₋₄)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms and aryl or heteroaryl is optionally substituted with one to two substituents independently selected from halo and cyano); R² is hydro, hydroxy, halo, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy (wherein alkyl is optionally substituted with one to three halo atoms); R³ is -C(O)R⁷ (wherein R⁷ is (C₁₋₆)alkyl, (C₃₋₆)cycloalkyl, di(C₁₋₄)alkylamino, N-(C₁₋₄)alkyl-N-(C₁₋₄)alkyloxyamino, (C₁₋₄)alkyl((C₁₋₄)alkyloxy)amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl or piperazin-1-yl); R⁴ is halo, hydroxy, cyano, (C₁₋₆)alkyl or (C₁₋₆)alkyloxy; and R⁵ is (C₁₋₆)alkyl; and the pharmaceutically acceptable salts and N-oxides thereof.

  本发明涉及式 I 的新型 α₁-肾上腺素受体拮抗剂： 其中 p 是 0 或 1； t 是 0、1 或 2 X 是 O、S 或 NR⁶（其中 R⁶ 是氢或 (C₁₋₆)烷基）； Y 和 Z 独立地为 CH 或 N； R¹是氢、羟基、卤代、硝基、氨基、氰基、(C₁₋₄)烷硫基、乙酰氨基、三氟乙酰氨基、甲磺酰氨基、(C₁₋₆)烷基、(C₃₋₆)环烷基、(C₃₋₆)环烷基(C₁₋₄)烷基、噁唑-2-基、芳基、杂芳基、芳基(C₁₋₄)烷基、杂芳基(C₁₋₄)烷基、(C₁₋₆)烷氧基、(C₃₋₆)环烷氧基、(C₃₋₆)环烷基(C₁₋₄)烷氧基，2-丙炔氧基，芳基氧基，杂芳基氧基、芳基（C₁₋₄）烷氧基或杂芳基（C₁₋₄）烷氧基（其中烷基任选被一至三个卤原子取代，芳基或杂芳基任选被一至两个独立选自卤素和氰基的取代基取代）； R² 是氢、羟基、卤代、氰基、(C₁₋₆)烷基或(C₁₋₆)烷氧基（其中烷基任选被一至三个卤原子取代）； R³ 是 -C(O)R⁷（其中 R⁷ 是 (C₁₋₆)烷基、(C₃₋₆)环烷基、二(C₁₋₄)烷基氨基、N-(C₁₋₄)烷基-N-(C₁₋₄)烷氧基氨基、(C₁₋₄)烷基((C₁₋₄烷氧基)氨基、吡咯烷-1-基、哌啶-1-基、吗啉-4-基或哌嗪-1-基)； R⁴ 是卤素、羟基、氰基、(C₁₋₆)烷基或 (C₁₋₆)烷氧基；和 R⁵ 是 (C₁₋₆)烷基；及其药学上可接受的盐和 N-氧化物。
• SELECTED BENZOFURAN DERIVATIVES
  申请人：Arpida AG

  公开号：EP1838704A1

  公开（公告）日：2007-10-03
• US5688795A
  申请人：——

  公开号：US5688795A

  公开（公告）日：1997-11-18