N-(2-Cyanoethyl)-4-methylbenzamide | 22192-83-2

• 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: N-(2-Cyanoethyl)-4-methylbenzamide
• 英文别名: 3-(p-toluyl-amino)-propionitrile；3-(p-Methyl-benzoyl-amino)-propionitril
• CAS: 22192-83-2
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00456770
• 分子量: 188.229
• InChiKey: QPMZYDIUEFNPKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-Cyanoethyl)-4-methylbenzamide 在 氨 作用下， 以 乙醇 为溶剂， 生成 3-(p-Methyl-benzoyl-amino)-propionamidin
  参考文献：
  名称：

  Syntheses of 2-Acylaminoacetamidine and 3-Acylaminopropionamidine Derivatives

  摘要：

  为了检测它们的抗病毒活性，通过相应的腈类经由乙基咪唑合成2-酰氨基乙脒（II）和3-酰氨基丙脒盐酸盐（III）。假设了乙基2-酰氨基乙咪唑和乙基3-酰氨基丙咪唑在酰胺化过程中的反应活性差异。通过参考相应的单氰单酯（ethyl p-(N-cyanoethylcarbamoyl) benzoate）（XXI）的红外光谱，讨论了二氰（对-氰基）苯甲酰胺丙腈（XVIII）的亚胺酯化。其中，3-（对-甲基）苯甲酰胺丙脒盐酸盐被发现对小鼠和膜培养中的流感病毒具有抑制作用。

  DOI：

  10.1248/cpb.16.2355
• 作为产物：
  描述：

  对甲基苯甲酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 N-(2-Cyanoethyl)-4-methylbenzamide
  参考文献：
  名称：

  Three synthetic routes to a sterically hindered tetrazole. A new one-step mild conversion of an amide into a tetrazole

  摘要：

  5-[4'-Methyl-1,1'-biphenyl-2-yl]-1H-tetrazole (6), which contains a sterically hindered o-tetrazole group, was synthesized by three different routes, one of them employing a new tetrazole synthesis. The first involved the reaction of trialkyltin azides with 4'-methyl-1,1'-biphenyl-2-carbonitrile (3). The resultant trimethyltin-tetrazole adduct could be hydrolyzed with acid to yield biphenylytetrazole 6. The tri-n-butyltin-tetrazole adduct, however, was transformed into the corresponding N-trityl-protected tetrazole 5 to permit removal of the organic soluble tri-n-butyltin byproducts. The trityl group also permits 5 to be brominated at the benzylic position and then alkylated by imidazole derivatives. Subsequent acid hydrolysis of the trityl protecting group of 5 yielded biphenylyltetrazole 6. The second synthesis involved the nitrosation of an N-(2-cyanoethyl)-protected biphenylamidrazone 10 using N2O4 (g) to yield N-(2-cyanoethyl)-protected tetrazole 12. Aqueous base removes the cyanoethyl protecting group to yield biphenylyltetrazole 6. The third method involves the novel transformation of an N-(2-cyanoethyl)-substituted amide into the corresponding N-(2-cyanoethyl)-protected tetrazole in one step using triphenylphosphine, diethyl azodicarboxylate (DEAD), and azidotrimethylsilane. Subsequent base hydrolysis of the cyanoethyl group yielded 6 as before. Examples are also provided of the application of this new reaction to other N-(2-cyanoethyl)-protected carboxamides.

  DOI：

  10.1021/jo00007a027

文献信息

• Quinazolinamide derivatives
  申请人：Eggenweiler Hans-Michael

  公开号：US20100234324A1

  公开（公告）日：2010-09-16

  Novel quinazolinamide derivatives of the formula (I), in which R 1 -R 3 have the meanings indicated in Claim 1, are HSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

  新型喹唑啉酰胺衍生物的化学式（I），其中R1-R3具有权利要求书中指示的含义，是HSP90抑制剂，可用于制备用于治疗HSP90在疾病的抑制、调节和/或调控中发挥作用的药物。
• 8-Substituted isoquinoline derivative and the use thereof
  申请人：Kaneko Shunsuke

  公开号：US20100261701A1

  公开（公告）日：2010-10-14

  The present invention relates to a compound represented by the following formula (1): wherein D 1 , A 1 , D 2 , R 1 , D 3 , and R 2 each have the same meaning as defined in the present specification or a salt thereof. The compound represented by the formula (1) or a salt thereof has an IKKβ inhibiting activity and the like and is useful for the prevention and/or treatment of IKKβ-associated diseases or symptoms and the like.

  本发明涉及一种由以下式（1）表示的化合物： 其中D1，A1，D2，R1，D3和R2分别具有与本说明书中定义的相同含义或其盐。由式（1）表示的化合物或其盐具有IKKβ抑制活性等，对于预防和/或治疗IKKβ相关疾病或症状等方面是有用的。
• Aminocarbonyl-substituted benzimidazoles having tryptase-inhibitory activity
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US06512000B1

  公开（公告）日：2003-01-28

  A method for treating diseases in which tryptase inhibitors may be of thereapeutic value, which comprises the administration of a thereapeutic amount of a compound of the formula   The invention also comprises novel compounds of the formula (I). Exemplary is 2-[2-(4-amidinophenyl)ethyl]-1-methyl-benzimidazol-5-yl-carboxylic acid-N-(pyridin-3-yl-methyl)-N-methyl-amide-hydrochloride.

  一种用于治疗疾病的方法，其中组胺酶抑制剂可能具有治疗价值，包括给予公式的化合物的治疗剂量。该发明还包括公式（I）的新化合物。示例是2-[2-(4-氨基苯基)乙基]-1-甲基-苯并咪唑-5-基-羧酸-N-(吡啶-3-基甲基)-N-甲基酰胺盐酸盐。
• 8-SUBSTITUTED ISOQUINOLINE DERIVATIVE AND USE THEREOF
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP2366699A1

  公开（公告）日：2011-09-21

  The present invention relates to a compound represented by the following formula (1): wherein D1, A1, D2, R1, D3, and R2 each have the same meaning as defined in the present specification or a salt thereof. The compound represented by the formula (1) or a salt thereof has an IKKβ inhibiting activity and the like and is useful for the prevention and/or treatment of IKKβ-associated diseases or symptoms and the like.

  本发明涉及下式（1）所代表的化合物： 其中 D1、A1、D2、R1、D3 和 R2 各具有与本说明书中定义相同的含义或其盐。式（1）代表的化合物或其盐具有 IKKβ 抑制活性等，可用于预防和/或治疗 IKKβ 相关疾病或症状等。
• DUNCIA, JOHN V.;PIERCE, MICHAEL E.;SANTELLA, JOSEPH B. (III), J. ORG. CHEM., 56,(1991) N, C. 2395-2400
  作者：DUNCIA, JOHN V.、PIERCE, MICHAEL E.、SANTELLA, JOSEPH B. (III)

  DOI：——

  日期：——