N-<6-hydroxy<1,1'-biphenyl>-3-yl>acetamide | 29785-41-9

• 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-<6-hydroxy<1,1'-biphenyl>-3-yl>acetamide
• 英文别名: N-Acetyl-2-hydroxy-5-aminobiphenyl；2-hydroxy-5-acetamidobiphenyl；4-hydroxy-3-phenylacetanilide；N-(6-hydroxy-biphenyl-3-yl)-acetamide；N-(6-Hydroxy-biphenyl-3-yl)-acetamid；5-Acetamino-biphenylol-(2)；N-(4-hydroxy-3-phenylphenyl)acetamide
• CAS: 29785-41-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: LXMKOQSEWRFPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<6-hydroxy<1,1'-biphenyl>-3-yl>acetamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(tert-Butylamino-methyl)-5-(7-chloro-1-oxy-quinolin-4-ylamino)-biphenyl-2-ol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  邻苯基苯酚 在 palladium on activated charcoal 氢气 、 硝酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 16.0h， 生成 N-<6-hydroxy<1,1'-biphenyl>-3-yl>acetamide
  参考文献：
  名称：

  Catalysis of the Photo-Fries Reaction:  Antibody-Mediated Stabilization of High Energy States

  摘要：

  A conformationally constrained hapten is presented that is capable of catalyzing the first antibody-mediated photo-Fries rearrangement. In this reaction, absorption of light energy by a diphenyl ether substrate results in homolytic C-O bond cleavage followed by recombination to yield biphenyl-derived products. The most proficient antibody studied converts 4-phenoxyaniline 15 into 2-hydroxy-5-aminobiphenyl 16 under high-intensity irradiation at a rate of 8.6 muM/min. These results support a recent hypothesis stating that immunization with conformationally constrained haptens provides higher titers for the acquisition of simple binding antibodies; however, in this case, conformational constraint does not ensure the development of more efficient catalysts. Using the obtained antibodies, the presence of products resulting from escape of free radicals from the solvent cage can be suppressed, altering the excited state energy surface such that free radicals are funneled into the formation of the desired biphenyl product. However, studies also show the inactivation of the antibodies as a result of photodecay of the biphenyl product. Using an isocyanate scavenging resin, the photodecay product could be removed and the inactivation of the antibody drastically reduced. Furthermore, despite the observed photodecay, turnover of the antibody was present; this represents the first case in which true turnover of a photochemical reaction using a catalytic antibody could be observed.

  DOI：

  10.1021/ja038016n

文献信息

• Aminoalkylphenols as Antimalarials. II.¹ (Heterocyclic-amino)-α-amino-o-cresols. The Synthesis of Camoquin²
  作者：J. H. Burckhalter、F. H. Tendick、Eldon M. Jones、Patricia A. Jones、W. F. Holcomb、A. L. Rawlins

  DOI：10.1021/ja01184a023

  日期：1948.4
• The electrochemical preparation and kinetic and product studies of acylated quinol and quinol ether imines. In search of the hydrolysis products of the ultimate carcinogen of N-acetyl-2-aminofluorene
  作者：Michael Novak、John S. Helmick、Nicholas Oberlies、Kanchugarakoppal S. Rangappa、William M. Clark、John S. Swenton

  DOI：10.1021/jo00056a019

  日期：1993.2

  The N-acetyl and benzoyl derivatives of 4-methoxy-4-phenyl-2,5-cyclohexadienone imine and the N-benzoyl derivative of 4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1a-c) have been prepared via anodic oxidation of the corresponding amide of 4-aminobiphenyl in either methanol or water/acetonitrile, respectively. The products and the kinetics of the acidic and basic hydrolyses of these compounds were studied and the results compared with other N-acylquinol imine derivatives, including N-acetyl-4-hydroxy-4-phenyl-2,5-cyclohexadienone imine (1d), generated by solvolytic routes. The chemistry of these compounds was dependent upon the pH and the substituents on the quinol imine derivative. The major reaction pathways were hydrolysis of the imine linkage to afford the respective dienone and phenyl migration to afford the amides of 2-hydroxy- or 2-methoxy-5-aminobiphenyl. The reactivity of the quinol imine derivatives follows the order: 4-hydroxyl more reactive than 4-methoxyl compounds and N-acetyl more reactive than N-benzoyl derivatives. The higher reactivity for the former compounds is attributed to the greater electron-donating ability of the 4-hydroxyl versus the 4-methoxyl group. The higher reactivity of the N-acetyl relative to the N-benzoyl derivatives is attributed to the ca. 30-fold increase in basicity of the N-acetyl functionality. The additive effect of the 4-hydroxyl and N-acetyl functionality on the basic quinol imine moiety makes compounds having both of the groups difficult to isolate in aqueous media. This serves as a limitation for the preparation of the quinol imine derivative of N-acetyl-2-aminofluorene via the anodic oxidation methods reported herein.
• Diphenyl derivatives
  申请人：SQUIBB & SONS INC

  公开号：US02073683A1

  公开（公告）日：1937-03-16
• Synthesis and antifilarial activity of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]-2-pyrimidinyl]-N'-phenylguanidines
  作者：Mario Angelo、Daniel Ortwine、Donald Worth、Leslie M. Werbel、John W. McCall

  DOI：10.1021/jm00363a010

  日期：1983.9

  A series of N-[4-[[4-alkoxy-3-[(dialkylamino)methyl]phenyl]amino]- 2-pyrimidinyl]-N'-phenylguanidines have been synthesized for antifilarial evaluation. Reaction of the appropriate benzenamines with N-cyanoguanidine, followed by condensation of the resultant N-phenylimidodicarbonimidic diamides (V) with ethyl 4,4,4-trifluoro-3-oxobutanoate provided the intermediate N-(4-hydroxy-2-pyrimidinyl)-N'-phenylguanidines VIa. Alternatively, compounds VIa were synthesized by reaction of the requisite beta-keto esters (VII) with N-cyanoguanidine to give the (4-hydroxy-2-pyrimidinyl)cyanamides (VIII), followed by treatment with the desired benzenamines. Chlorination with POCl3 and condensation with the appropriate benzenamines (IX) generated the desired guanidines (X). Antifilarial activity was confined to adult Litomosoides carinii infections, and a structure-activity relationship for this activity is discussed. Lack of activity against L. carinii microfilaria and adult Brugia pahangi infections preclude further work in this area pending evaluation in additional experimental models.
• Adriaan Davidse; Kahley, Mary Jo; McClelland, Robert A., Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4513 - 4514
  作者：Adriaan Davidse、Kahley, Mary Jo、McClelland, Robert A.、Novak, Michael

  DOI：——

  日期：——