2-羟基-N-[4-[(2-羟基苯甲酰基)氨基]丁基]苯甲酰胺 | 76218-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-N-[4-[(2-羟基苯甲酰基)氨基]丁基]苯甲酰胺
• 英文名称: N,N’-(butane-1,4-diyl)bis(2-hydroxybenzamide)
• 英文别名: Benzamide, N,N'-1,4-butanediylbis(2-hydroxy-；2-hydroxy-N-[4-[(2-hydroxybenzoyl)amino]butyl]benzamide
• CAS: 76218-89-8
• 化学式: C₁₈H₂₀N₂O₄
• mdl: MFCD01666943
• 分子量: 328.368
• InChiKey: WIKQEUHLUWLDPP-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: methanol (67-56-1))
• 沸点：
  634.3±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-N-[4-[(2-羟基苯甲酰基)氨基]丁基]苯甲酰胺 、 二氯乙醚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到2,5,8-Trioxa-16,21-diaza-tricyclo[21.4.0.0^9,14]heptacosa-1(27),9(14),10,12,23,25-hexaene-15,22-dione
  参考文献：
  名称：

  A Convenient Method for Preparing Some New Macrocyclic Diamides

  摘要：

  开发了一种简单方便的方法，用于制备包含两个硫原子或两个到四个氧原子的不同环尺寸的宏环二酰胺。该两步法仅由反应水杨酸或2-巯基苯甲酸与各种二胺组成，随后进行威廉逊合成。

  DOI：

  10.1055/s-1994-25466
• 作为产物：
  描述：

  2-phenylmethoxy-N-[4-[(2-phenylmethoxybenzoyl)amino]butyl]benzamide 在 30 wt % Pd/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 以99%的产率得到2-羟基-N-[4-[(2-羟基苯甲酰基)氨基]丁基]苯甲酰胺
  参考文献：
  名称：

  Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors

  摘要：

  Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV.Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties.The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.033

文献信息

• Synthesis of New Benzo-substituted Macrocyclic Ligands Containing Pyridine or Triazole as Subcyclic Units
  作者：Ahmed H.M Elwahy、Ashraf A Abbas

  DOI：10.1016/s0040-4020(99)01068-6

  日期：2000.2

  The macrocyclic diamides 11–21, 42 and 43 were prepared by nucleophilic reaction of the bis phenols 22–29 with the appropriate dihalo compounds 2, 3, 40 and 41, respectively. The macrocyclic dithiodiamides 30–33 were obtained in good yields upon treatment of 11, 13, 15 and 17 with Lawesson's reagent. The macrocycles 61–63 were prepared by condensation of the bis(aldehyde) 37 with the appropriate bis(aminotriazoles)

  大环二酰胺11 - 21，42和43是由双酚的亲核反应而制备22 - 29用适当的二卤代化合物2，3，40和41分别。大环dithiodiamides 30 - 33在处理后的良好的产率得到11，13，15和17与Lawesson试剂。大环61 – 63是通过双（醛）缩合制备的37用适当的双（氨基三唑）50 – 54生成相应的席夫碱56 – 60，然后用NaBH 4还原。
• New compounds: N-1, N8-bis(2, 3-dihydroxybenzoyl)spermidine and analogs as potential iron-chelating drugs
  作者：K.K. Bhargava、R.W. Grady、A. Cerami

  DOI：10.1002/jps.2600690836

  日期：1980.8

  N1,N8-bis(2,3-dihydroxybenzoyl)spermidine was synthesized and evaluated as an iron-chelating drug. Homologs were prepared and evaluated together with a series of N,N'-bis(2,3-dihydroxybenzoyl)-alpha,omega-diaminoalkanes. Analogous 2-hydroxbenzoyl compounds also were synthesized and evaluated.

  合成了N1，N8-双（2,3-二羟基苯甲酰基）亚精胺，并将其评价为铁螯合剂。制备同源物并与一系列N，N′-双（2，3-二羟基苯甲酰基）-α，ω-二氨基烷烃一起评估。还合成和评估了类似的2-羟基苯甲酰基化合物。
• Synthesis of novel amide-crownophanes and Schiff base-crownophanes based on<i>p</i>-phenylene, 2,6-naphthalene, and 9,10-anthracene
  作者：Hussni A. Muathen、Nour A. M. Aloweiny、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.129

  日期：2009.7

  The novel macrocyclic diamides , are obtained in 45–66% yields by the reaction of dipotassium salts and with each of 1,4-di(bromomethyl)benzene , 2,6-di(bromomethyl)naphthalene and 9,10-di(bromomethyl)anthracene , repectively, in boiling DMF. On the other hand, the new macrocyclic Schiff bases and are obtained in 44% and 42% yields by heating the appropriate bis-amines , with the corresponding bis-aldehydes

  新型大环二酰胺 ， 通过二钾盐的反应获得45-66％的收率 和 与每个 1,4-二（溴甲基）苯 ， 2,6-二（溴甲基）萘 和 9,10-二（溴甲基）蒽 分别在沸腾的DMF中。另一方面，新的大环席夫碱 和 通过加热适当的双胺可得到44％和42％的收率 ， 与相应的双醛 ， 分别在高稀释条件下于回流乙酸中。J.杂环化​​学。（2009）。
• Synthesis of mixed-donor azaoxathia macrocyclic tetraamides, acyclic polyether di/and tetraamides and their C-pivot lariat derivatives
  作者：Ashraf A. Abbas

  DOI：10.1002/jhet.5570440322

  日期：2007.5

  The macrocyclic tetraamides 11a-e and 15-hydroxy macrocyclic tetraamides 23a-c were prepared in good yields by the nucleophilic reaction of the potassium salts of the bis-phenoles 10a-c with the appropriate dihalo compounds 5a-d and 15. Moreover, the acyclic diamides 7, 9, 17-21 and bis-acyclic tetraamide 22 were obtained in high yields by the reaction of the appropriate dichloro compounds with different

  大环tetraamides 11A-E和15-羟基大环tetraamides 23A-C是由双：酚的钾盐的亲核反应以良好的收率制备10a到10c与适当的二卤代化合物5A-d和15此外，非环状二酰胺7，9，17-21和双-无环四酰胺22以高产率通过用不同的酚胺和仲胺的合适的二氯化合物的反应制得。用不同的酰氯酰化23a-c，得到相应的酯24a-c。化合物24a-c与不同的仲胺反应，以高收率得到相应的新型套索大环化合物25a-d。
• Synthesis of Novel Benzo-substituted Macrocyclic Ligands Containing Thienothiophene Subunits
  作者：Ahmed E. M. Mekky、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.2012

  日期：2014.8

  A facile synthetic approach was adopted toward the synthesis of benzo-fused macrocyclic ligands with thienothiophene group incorporated into the ring system. Thus, treatment of bis(bromomethyl) compound with the K salt of the appropriate bis(phenol)s in boiling DMF led to the formation of the novel macrocyclic diamides in 39–58% yield. Reaction of with the potassium salt (obtained upon treatment of

  采用一种简便的合成方法来合成苯并噻吩基并入环系统的苯并稠合的大环配体。因此，双（溴甲基）化合物的处理 与适当的双（酚）的K盐 在沸腾的DMF中导致形成新的大环二酰胺 收率为39–58％。的反应 与钾盐（经治疗 水杨醛 在回流的DMF中用乙醇氢氧化钾溶液制得新型双（醛） 收率73％。环合的 与适当的双（N-取代）氰基乙酰胺衍生物 和 提供了目标大环 和 分别达到48％和55％的产量。双醛的反应 与1,3-和1,4-二氨基丙烷 和 在高稀释条件下于回流乙醇中制得相应的大环席夫碱 和 分别有41％和37％的产量。环合的 与1,3-双（4-氨基-5-苯基-3-基硫烷基甲基）丙烷（）在冰醋酸中在高稀释条件下得到大环席夫碱收率为46％。另一方面，双（醛）的环缩合 和 与3,4-双（4-氨基-5-苯基-3-基硫烷基甲基）噻吩并噻吩 在高稀释条件下于回流乙酸中意外地获得了新型缩合的大环杂环化合物 和 分别为33％和28％。新型双（胺）