3-[(3-硝基-2-吡啶基)氨基]丙酸乙酯 | 136742-53-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-[(3-硝基-2-吡啶基)氨基]丙酸乙酯
• 英文名称: ethyl 3-[(3-nitropyridin-2-yl)amino]propionate
• 英文别名: 3-[(3-nitro-2-pyridinyl)amino]propanoic acid ethyl ester；ethyl 3-((3-nitro-pyridin-2-yl)amino)propanoate；ethyl 3-[(3-nitropyridin-2-yl)amino]propanoate
• CAS: 136742-53-5
• 化学式: C₁₀H₁₃N₃O₄
• mdl: MFCD15490086
• 分子量: 239.231
• InChiKey: VBBRZXNGRQFAJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(3-硝基-2-吡啶基)氨基]丙酸乙酯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-[[3-[(4-chlorobenzoyl)amino]-2-pyridinyl]amino]propanoic acid ethyl ester
  参考文献：
  名称：

  2-Phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides as nonbenzodiazepine anticonvulsants and anxiolytics

  摘要：

  A series of 2-phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides were designed and synthesized as non-benzodiazepine anxiolytics based on a molecular disconnection of a typical 1,4-benzodiazepine (BZD). A number of these compounds showed submicromolar potency in a [H-3]benzodiazepine binding assay in vitro and good potency in protecting rodents against pentylenetetrazole-induced seizures. Compound 84 appears to be a selective anticonvulsant (pentylenetetrazole) agent when tested against a profile of chemically and electrically induced seizures in mice. In addition, compound 148 appears to be a selective anxiolytic/hypnotic agent on the basis of biochemical and pharmacological characterization. It appears to be a full BZD agonist as assessed by GABA shift ratio and to be effective in punishment and nonpunishment animal models of anxiety. In addition, it shows a lower side-effect profile than diazepam as assessed by rotorod neurotoxicity and potentiation of ethanol-induced sleep time in mice. The chemistry and structure-activity relationships of this series is discussed.

  DOI：

  10.1021/jm00114a007
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 生成 3-[(3-硝基-2-吡啶基)氨基]丙酸乙酯
  参考文献：
  名称：

  TOMCZUK, BRUCE E.;SUTHERIAND, DEBORAH S.

  摘要：

  DOI：

文献信息

• Fused imidazoheterocyclic compounds and pharmaceutical compositions
  申请人：A. H. Robins Company, Inc.

  公开号：US04772600A1

  公开（公告）日：1988-09-20

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  咪唑杂环化合物的化学式为：##STR1## 其中A环是吡啶的四个位置中的任意一个；B是羰基、硫代甲基或羟甲基；Z是氢、卤素、较低烷基、羟基、较低烷氧基、二较低烷基氨基或硝基；Ar是苯基、吡啶基、噻吩基或呋喃基；W与B形成多种组合，包括酸、酯、醇、酰胺和酮。这些化合物在治疗活体动物身体的方法中具有中枢神经系统活性，可用作肌肉松弛剂、抗惊厥剂和抗焦虑剂。
• Method of treating animals using fused imidazoheterocyclic compounds
  申请人：A. H. Robins Company, Incorporated

  公开号：US04914109A1

  公开（公告）日：1990-04-03

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  具有以下式子的咪唑杂环化合物：##STR1## 其中A环是吡啶，可以在其四个位置中的任何一个；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，低碳基，羟基，低碳氧基，二低碳基氨基或硝基；Ar是苯基，吡啶基，噻吩基或呋喃基；W与B形成各种各样的基团组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物身体的肌肉松弛剂，抗癫痫剂和抗焦虑剂的方法中具有中枢神经系统活性。
• Pharmaceutical method using fused imidazoheterocyclic compounds
  申请人：A. H. Robins Company, Incorporated

  公开号：US04948800A1

  公开（公告）日：1990-08-14

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  具有以下式子的咪唑杂环化合物：##STR1## 其中A环是吡啶，可以位于其四个位置之一；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，低烷基，羟基，低烷氧基，二低烷基氨基或硝基；Ar是苯基，吡啶基，噻吩基或呋喃基；W与B形成广泛的基团组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物身体作为肌肉松弛剂，抗癫痫剂和抗焦虑剂的方法中具有中枢神经系统活性。
• Fused imidazopyridine compounds
  申请人：A. H. Robins Company, Incorporated

  公开号：US04824951A1

  公开（公告）日：1989-04-25

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  具有以下式子的咪唑杂环化合物：##STR1## 其中A环是吡啶，可以在其四个位置中的任意一个；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，较低的烷基，羟基，较低的烷氧基，二较低烷基氨基或硝基；Ar是苯基，吡啶基，噻吩基或呋喃基；W与B形成广泛的组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物体作为肌肉松弛剂，抗惊厥剂和抗焦虑剂时具有中枢神经系统活性。
• Novel compounds with renin-inhibiting activity
  申请人：Beecham Group p.l.c.

  公开号：EP0416740A2

  公开（公告）日：1991-03-13

  Compounds of formula (I), and pharmaceutically acceptable salts thereof: wherein the Het ring is of sub-formula (a) or (b): wherein one or two of W₁, W₂, W₃ and W₄ is N or NO (such that if two are NO then these are W₁ and W₄), and the others are CH, CRa or CRb; one of Q₁, Q₂ and Q₃ is S and the other two are CH and CRc; either Z₁ and Z₂ are absent and Z₃, Z₄ and Z₅ and the carbon atoms to which Z₃ and Z₅ are attached, form a 5-membered non-aromatic heterocyclic ring; or Z₁ is absent and Z₂, Z₃, Z₄, Z₅ and the carbon atoms to which Z₂ and Z₅ are attached, form a 6-membered non-aromatic heterocyclic ring; or Z₁, Z₂, Z₃, Z₄ and Z₅ and the carbon atoms to which Z₁ and Z₅ are attached, form a 7-membered non-aromatic heterocyclic ring; E is absent or is (CH₂)n or CH(CH₂)n-1 wherein n is 1 to 4; A is -CONH-, -NHCO-, -COO-, -S(O)r- wherein r is 0, 1 or 2, or -CH₂-; p is 0, 1 or 2; s is 0, 1, 2, 3 or 4; q is 0 or 1; Rz is hydrogen, C₁₋₆ alkyl or, when A is -CH₂-, hydroxy; Ra and Rb are independently selected from hydrogen or a substituent; R₁ is CH₂R₉ wherein R₉ is optionally substituted aryl or heteroaryl; R₂ is CHR₁₀R₁₁ wherein R₁₀ is hydrogen or methyl and R₁₁ is C₁₋₆ alkyl, C₃₋₈ cycloalkyl, optionally substituted aryl or heteroaryl, or R₁₁ is amino, C₂₋₇ alkanoylamino, 2-oxopyrrolidinyl, 2-oxopiperidinyl or C₁₋₆ alkoxycarbonylamino; R₃ is CH₂R₁₂ wherein R₁₂ is C₁₋₆ alkyl, C₃₋₈cycloalkyl or phenyl; R₄ is C₁₋₆ alkyl, C₃₋₈ cycloalkyl, a saturated or unsaturated heterocyclic ring linked through carbon, hydroxy, C₁₋₆ alkoxy, C₁₋₇ alkanoyloxy, amino, C₁₋₇ alkanoylamino, amino substituted by one or two C₁₋₆ alkyl groups, or C₁₋₆ alkylsulphonyl, carboxy, C₁₋₆ alkoxycarbonyl, benzyloxycarbonyl, aminocarbonyl or CH(NHR₁₃)CO₂R₁₄ wherein R₁₃ is hydrogen or C₁₋₆ alkanoyl and R₁₄ is hydrogen or C₁₋₆ alkyl; or (when s is 2 to 4) R₄ is a saturated or unsaturated heterocyclic ring linked through nitrogen; and the dashed line represents an optional bond (when E is present); which are renin inhibitors, a process for their preparation and their use as pharmaceuticals.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 Het 环属于子式（a）或（b）： 其中 W₁、W₂、W₃ 和 W₄ 中的一个或两个是 N 或 NO（这样，如果两个是 NO，那么它们就是 W₁ 和 W₄），其他的是 CH、CRa 或 CRb； Q₁、Q₂ 和 Q₃ 中有一个是 S，其他两个是 CH 和 CRc； Z₁ 和 Z₂ 不存在，且 Z₃、Z₄ 和 Z₅ 与 Z₃ 和 Z₅ 所连接的碳原子形成一个 5 元非芳杂环；或 Z₁ 不存在，且 Z₂、Z₃、Z₄、Z₅ 与 Z₂ 和 Z₅ 所连接的碳原子形成一个 6 元非芳杂环；或 Z₁、Z₂、Z₃、Z₄ 和 Z₅ 与 Z₁ 和 Z₅ 所连接的碳原子形成一个 7 元非芳杂环； E 不存在或为 (CH₂)n 或 CH(CH₂)n-1，其中 n 为 1 至 4； A 是-CONH-、-NHCO-、-COO-、-S(O)r-（其中 r 是 0、1 或 2）或-CH₂-； p 是 0、1 或 2； s 是 0、1、2、3 或 4； q 是 0 或 1； Rz 是氢、C₁₋₆烷基或（当 A 是-CH₂-时）羟基； Ra 和 Rb 分别独立地选自氢或取代基； R₁ 是 CH₂R₉，其中 R₉ 是任选取代的芳基或杂芳基； R₂ 是 CHR₁₀R₁₁ 其中 R₁₀ 是氢或甲基，R₁₁ 是 C₁₋₆ 烷基、C₃₋₈ 环烷基、R₁₁是氨基、C₂₋₇烷酰氨基、2-氧代吡咯烷基、2-氧代哌啶基或 C₁₋₆烷氧羰基氨基； R₃ 是 CH₂R₁₂，其中 R₁₂ 是 C₁₋₆ 烷基、C₃₋₈ 环烷基或苯基； R₄ 是 C₁₋₆烷基、C₃₋₈环烷基、通过碳连接的饱和或不饱和杂环、羟基、C₁₋₆烷氧基、C₁₋₇烷酰氧基、氨基、C₁₋₇烷酰氨基、被一个或两个C₁₋₆烷基取代的氨基、或 C₁₋₆ 烷基磺酰基、羧基、C₁₋₆ 烷氧基羰基、苄氧羰基、氨基羰基或 CH(NHR₁₃)CO₂R₁₄ 其中 R₁₃ 是氢或 C₁₋₆ 烷酰基，R₁₄ 是氢或 C₁₋₆ 烷基；或（当 s 为 2 至 4 时）R₄ 是通过氮连接的饱和或不饱和杂环；以及 虚线代表任选键（当 E 存在时）； 它们是肾素抑制剂、其制备过程以及作为药物的用途。