furan-2-carboxylic acid-3-aminopropyl amide | 116784-81-7

• 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
• 英文名称: furan-2-carboxylic acid-3-aminopropyl amide
• 英文别名: Furan-2-carboxylic acid (3-amino-propyl)-amide；N-(3-aminopropyl)furan-2-carboxamide
• CAS: 116784-81-7
• 化学式: C₈H₁₂N₂O₂
• mdl: MFCD04542437
• 分子量: 168.195
• InChiKey: MSKZFRQYKIUIAL-UHFFFAOYSA-N

物化性质

• 沸点：
  370.6±22.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  68.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  furan-2-carboxylic acid-3-aminopropyl amide 、 2-氯-4-氨基-6,7-二甲氧基喹唑啉 以 异戊醇 为溶剂， 反应 36.0h， 以58%的产率得到Furan-2-carboxylic acid [3-(4-amino-6,7-dimethoxy-quinazolin-2-ylamino)-propyl]-amide; hydrochloride
  参考文献：
  名称：

  Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity

  摘要：

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.

  DOI：

  10.1021/jm00121a011
• 作为产物：
  描述：

  呋喃甲酰氯 、 1,3-丙二胺 在 氢溴酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 furan-2-carboxylic acid-3-aminopropyl amide
  参考文献：
  名称：

  Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity

  摘要：

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.

  DOI：

  10.1021/jm00121a011

文献信息

• GIARDINA, DARIO;BRASILI, LIVIO;GREGORY, MAURIZIO;MASSI, MAURIZIO;PICCHIO,+, J. MED. CHEM., 32,(1989) N, C. 50-55
  作者：GIARDINA, DARIO、BRASILI, LIVIO、GREGORY, MAURIZIO、MASSI, MAURIZIO、PICCHIO,+

  DOI：——

  日期：——
• LIQUID CRYSTAL ALIGNMENT AGENT, LIQUID CRYSTAL ALIGNMENT FILM, AND LIQUID CRYSTAL DISPLAY ELEMENT
  申请人：Chi Mei Corporation

  公开号：US20170152443A1

  公开（公告）日：2017-06-01

  A liquid crystal alignment agent allowing formation of an LCD element having good reliability and less residual image, a liquid crystal alignment film, and an LCD element having the liquid crystal alignment film are shown. The liquid crystal alignment agent includes a polymer (A), a photosensitive polysiloxane (B), and a solvent (C). The polymer (A) is obtained by reacting a mixture that includes a tetracarboxylic dianhydride component (a-1) and a diamine component (a-2). The photosensitive polysiloxane (B) is obtained by reacting a polysiloxane (b-1) having an epoxy group with a cinnamic acid derivative (b-2) and an aromatic heterocyclic derivative (b-3) containing nitride, oxide or sulfide.
• [EN] ANTIMICROBIAL COMPOSITIONS<br/>[FR] COMPOSITIONS ANTIMICROBIENNES
  申请人：SYMRISE AG

  公开号：WO2018068825A1

  公开（公告）日：2018-04-19

  The present invention is the use of a compound of formula (I) or a (pharmaceutically) acceptable salt thereof, wherein (a) X denotes CH=CH or CZ1=CZ2, wherein if Z1 is H then Z2 denotes a radical selected from the group consisting of OH, NH2, NHMe, NMe2, OMe and OEt and if Z2 is H then Z1 denotes a radical selected from the group consisting of OH, NH2, NHMe, NMe2, OMe and OEt, Y denotes a radical selected from the group consisting of NH2, NHMe, NMe2, NHEt, O-(CH2)n-OH, wherein n is 2 to 5 and R denotes a radical selected from the group consisting of H, OH, Me, Et, OMe, OEt, NH2, NHMe, NMe2, NHEt and NEt2, or (b) X denotes O, Y denotes a radical selected from the group consisting of NH2, NHMe, NMe2, NHEt, O-(CH2)n-OH and OMe, wherein n is 2 to 5 and R denotes H, OH, Me, Et, OMe, OEt, NH2, NHMe, NMe2, NHEt, NEt2 as antimicrobial agent as well as to composition comprising said agent.
• Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity
  作者：Dario Giardina、Livio Brasili、Maurizio Gregori、Maurizio Massi、Maria T. Picchio、Wilma Quaglia、Carlo Melchiorre

  DOI：10.1021/jm00121a011

  日期：1989.1

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.