4-(2-dimethylamino)ethylene-5-nitropyridine | 64679-69-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-(2-dimethylamino)ethylene-5-nitropyridine
• 英文别名: dimethyl-[2-(3-nitro-pyridin-4-yl)-vinyl]-amine；N,N-Dimethyl-2-(3-nitropyridin-4-yl)ethen-1-amine；N,N-dimethyl-2-(3-nitropyridin-4-yl)ethenamine
• CAS: 64679-69-2
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: YYUSZTQRCCAPDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(2-dimethylamino)ethylene-5-nitropyridine 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 以3.19 g的产率得到3-硝基吡啶-4-甲醛
  参考文献：
  名称：

  Inhibition of c-Kit, VEGFR-2 (KDR), and ABCG2 by analogues of OSI-930

  摘要：

  The quinoline domain of OSI-930, a dual inhibitor of receptor tyrosine kinases (RTKs) c-Kit and KDR, was modified in an effort to further understand the SAR of OSI-930, and the binding site characteristics of c-Kit and KDR. A series of 16 compounds with heteroatom substituted pyridyl and phenyl ring systems was synthesized and evaluated against a panel of kinases including c-Kit and KDR. Aminopyridyl derivative 6 was found to be the most active member of the series with 91% and 57% inhibition of c-Kit at 10 mu M and 1 mu M, respectively and 88% and 50% inhibition of KDR at 10 mu M and 1 mu M, respectively. The target compounds were also tested for their ability to inhibit efflux of mitoxantrone through inhibition of ATP dependent ABCG2 pump. Nitropyridyl derivative 5 and o-nitrophenyl derivative 7 exhibited complete inhibition of the ABCG2 pump with IC50 values of 13.67 mu M and 16.67 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.070
• 作为产物：
  描述：

  3-硝基-4-甲基吡啶 、 N,N-二甲基甲酰胺二甲基缩醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以94%的产率得到4-(2-dimethylamino)ethylene-5-nitropyridine
  参考文献：
  名称：

  一种6-氮杂吲哚的制备方法

  摘要：

  本发明公开了一种6‑氮杂吲哚的制备方法，包括以下步骤：步骤一、先进行4‑(2‑二甲氨基)乙烯‑5‑硝基吡啶的制备：在1L圆底在烧瓶中加入干燥290mL DMF，然后加入27.6g与200mmol的4‑甲基‑3‑硝基吡啶和2.76g碳酸钾，搅拌下向其中加入26.6mL与2.2当量的二甲基甲酰胺二甲基乙缩醛；在氮气氛下将混合物加热至85‑95℃并搅拌6小时；反应结束，将反应冷却至室温并将溶液倒入500‑700mL水中；在真空条件下过滤深橙红色悬浮液，收集固体并在真空烘箱中干燥过夜。本6‑氮杂吲哚的制备方法，以4‑甲基‑2‑硝基吡啶为原料在碱性条件同DMF‑DMA发生缩合反应，然后以铁粉为还原剂在酸性条件下关环得6‑氮杂吲哚，本方法反应条件温和反应处理简单，收率高，适合工业生产。

  公开号：

  CN113980018A

文献信息

• [EN] HETEROCYCLIC AMIDE DERIVATIVES WHICH POSSES GLYCOGEN PHOSPHORYLASE INHIBITORY ACTIVITY<br/>[FR] DERIVES D'AMIDE HETEROCYCLIQUES AYANT UNE ACTIVITE INHIBITRICE DE LA GLYCOGENE PHOSPHORYLASE
  申请人：ASTRAZENECA AB

  公开号：WO2005020987A1

  公开（公告）日：2005-03-10

  Heterocyclic amides of formula (1) wherein: B is selected from R4 and R 5 together are either -S-C(R 6)=C(R 7)_ or _C(R7)=C(R6)_S_; A is a pyridylene ring; m is 0, 1 or 2; n is 0 or 1; R 2 is for example selected from (I -4C)alkyl, hydroxy(l -4C)alkyl, dihydroxy(2-4C)alkyl and (1 -4C)aIkoxy(1 -4C)alkyl. or a pharmaceutically acceptable salt possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives, intermediates in said processes and pharmaceutical compositions containing the heterocyclic amide derivatives are described.

  式（1）中的杂环酰胺，其中：B选自R4和R5，R4和R5一起是-S-C（R6）=C（R7）_或_C（R7）=C（R6）_S_；A是吡啶基环；m为0、1或2；n为0或1；R2例如选自（1-4C）烷基、羟基（1-4C）烷基、二羟基（2-4C）烷基和（1-4C）氧基（1-4C）烷基，或者是药学上可接受的盐，具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备所述杂环酰胺衍生物的方法、所述方法中的中间体以及含有所述杂环酰胺衍生物的药物组合物。
• Heterocyclic amide derivatives as inhibitors of glycogen phoshorylase
  申请人：Birch Martin Alan

  公开号：US20050131015A1

  公开（公告）日：2005-06-16

  Heterocyclic amides of formula (1) wherein: X is N or CH; R 4 and R 5 together are either —S—C(R 6 )═C(R 7 )— or —C(R 7 )═C(R 6 )—S—; R 6 and R 7 are independently selected from, for example hydrogen, halo and C l-4 alkyl; A is phenylene or heteroarylene; n is 0, 1 or 2; R 1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; R 2 is hydrogen, hydroxy or carboxy; R 3 is selected from for example hydrogen, hydroxy, aryl, heterocyclyl and C 1-4 alkyl(optionally substituted by 1 or 2 R 8 groups); R 8 is selected from for example hydroxy, —COCOOR 9 , —C(O)N(R 9 )(R 10 ), —NHC(O)R 9 , (R 9 )(R 10 )N— and —COOR 9 ; R 9 and R 10 are selected from for example hydrogen, hydroxy, C 1-4 alkyl (optionally substituted by 1 or 2 R 13 ); R 13 is selected from hydroxy, halo, trihalomethyl and C 1-4 alkoxy; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  公式（1）的杂环酰胺，其中：X是N或CH；R4和R5一起是—S—C(R6)═C(R7)—或—C(R7)═C(R6)—S—；R6和R7独立选择自氢、卤素和Cl-4烷基；A是苯基或杂环芳基；n为0、1或2；R1选择自卤素、硝基、氰基、羟基、羧基；R2是氢、羟基或羧基；R3选择自氢、羟基、芳基、杂环芳基和C1-4烷基（可选地取代1或2个R8基）；R8选择自羟基、—COCOOR9、—C（O）N（R9）（R10）、—NHC（O）R9、（R9）（R10）N—和—COOR9；R9和R10选择自氢、羟基、C1-4烷基（可选地取代1或2个R13）；R13选择自羟基、卤素、三卤甲基和C1-4烷氧基；或其药学上可接受的盐或前药；具有糖原磷酸化酶抑制活性，因此在治疗与增加的糖原磷酸化酶活性相关的疾病状态中具有价值。还描述了制造该杂环酰胺衍生物的过程以及含有它们的制药组合物。
• HETEROCYCLIC AMIDE DERIVATIVES AS INHIBITORS OF GLYCOGEN PHOSPHORYLASE
  申请人：Birch Martin Alan

  公开号：US20070043069A1

  公开（公告）日：2007-02-22

  Heterocyclic amides of formula (1) wherein: X is N or CH; R 4 and R 5 together are either —S—C(R 6 )═C(R 7 )— or —C(R 7 )═C(R 6 )—S—; R 6 and R 7 are independently selected from, for example hydrogen, halo and C 1-4 alkyl; A is phenylene or heteroarylene; n is 0, 1 or 2; R 1 is selected from for example halo, nitro, cyano, hydroxy, carboxy; R 2 is hydrogen, hydroxy or carboxy; R 3 is selected from for example hydrogen, hydroxy, aryl, heterocyclyl and C 1-4 alkyl(optionally substituted by 1 or 2 R 8 groups); R 8 is selected from for example hydroxy, —COCOOR 9 , —C(O)N(R 9 )(R 10 ), —NHC(O)R 9 , (R 9 )(R 10 )N— and —COOR 9 ; R 9 and R 10 are selected from for example hydrogen, hydroxy, C 1-4 alkyl (optionally substituted by 1 or 2 R 13 ); R 13 is selected from hydroxy, halo, trihalomethyl and C 1-4 alkoxy; or a pharmaceutically acceptable salt or pro-drug thereof, possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  式（1）的杂环酰胺，其中：X为N或CH；R4和R5组合在一起是—S—C(R6)═C(R7)—或—C(R7)═C(R6)—S—；R6和R7独立选择自例如氢、卤素和C1-4烷基；A为苯撑或杂芳撑；n为0、1或2；R1选择自例如卤素、硝基、氰基、羟基、羧基；R2为氢、羟基或羧基；R3选择自例如氢、羟基、芳基、杂环基和C1-4烷基（可以选择性地被1或2个R8基取代）；R8选择自例如羟基、—COCOOR9、—C(O)N(R9)(R10)、—NHC(O)R9、(R9)(R10)N—和—COOR9；R9和R10选择自例如氢、羟基、C1-4烷基（可以选择性地被1或2个R13取代）；R13选择自羟基、卤素、三卤甲基和C1-4烷氧基；或其药学上可接受的盐或前药具有糖原磷酸化酶抑制活性，因此在治疗与增加的糖原磷酸化酶活性相关的疾病状态方面具有价值。描述了制备该杂环酰胺衍生物的方法和含有它们的药物组合物。
• Tetrahydroquinolones and Aza-Analogues Thereof for Use as Dpp-IV Inhibitors in the Treatment of Diabetes
  申请人：Birch Martin Alan

  公开号：US20080009512A1

  公开（公告）日：2008-01-10

  Compound of formula (I) or a pharmaceutically-acceptable salt thereof, formula (I) wherein Ar is optionally substituted phenyl; R 1 is selected from: formula a) or b) (wherein is a single or double bond); R 5 , R 6 , R 7 and R 8 are for or alkyl; R 4 is selected from hydrogen, (3-4C)cycloalkyl and optionally substituted (1-4C)alkyl; R 10 is for example selected from hydrogen, (1-4C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl, hydroxy(1-4C)alkyl, (1-4C)alkoxy, aryl(1-4C)alkyl; Y is carbon and Ring A is optionally substituted phenylene; or each Y may independently be carbon or nitrogen and Ring A is optionally substituted 5- or 6-membered, heteroarylene ring; R 11 is selected from hydrogen and optionally substituted phenyl; p is independently at each occurrence 0, 1 or 2; are described. Processes for making such compounds and their use as DPP-IV inhibitors in the treatment of diabetes are also described.

  化合物的公式（I）或其药学上可接受的盐，公式（I）中 Ar 是可选的取代苯基；R1 选自：公式 a）或 b）（其中是单键或双键）；R5、R6、R7 和 R8 是氢或烷基；R4 选自氢、（3-4C）环烷基和可选取代的（1-4C）烷基；R10 例如选自氢、（1-4C）烷基、（3-6C）环烷基（1-4C）烷基、羟基（1-4C）烷基、（1-4C）烷氧基、芳基（1-4C）烷基；Y 是碳且环A是可选的取代苯基；或每个Y可以独立地是碳或氮，环A是可选的取代5-或6-成员的杂环芳烃环；R11选自氢和可选取代的苯基；p 在每次出现时独立地为0、1或2。描述了制备这种化合物的过程以及它们作为DPP-IV抑制剂在糖尿病治疗中的用途。
• 一种6-氮杂吲哚的制备方法
  申请人：苏州艾缇克药物化学有限公司

  公开号：CN113980018A

  公开（公告）日：2022-01-28

  本发明公开了一种6‑氮杂吲哚的制备方法，包括以下步骤：步骤一、先进行4‑(2‑二甲氨基)乙烯‑5‑硝基吡啶的制备：在1L圆底在烧瓶中加入干燥290mL DMF，然后加入27.6g与200mmol的4‑甲基‑3‑硝基吡啶和2.76g碳酸钾，搅拌下向其中加入26.6mL与2.2当量的二甲基甲酰胺二甲基乙缩醛；在氮气氛下将混合物加热至85‑95℃并搅拌6小时；反应结束，将反应冷却至室温并将溶液倒入500‑700mL水中；在真空条件下过滤深橙红色悬浮液，收集固体并在真空烘箱中干燥过夜。本6‑氮杂吲哚的制备方法，以4‑甲基‑2‑硝基吡啶为原料在碱性条件同DMF‑DMA发生缩合反应，然后以铁粉为还原剂在酸性条件下关环得6‑氮杂吲哚，本方法反应条件温和反应处理简单，收率高，适合工业生产。