4-(4-Hydroxyphenyl)semicarbazide | 73469-92-8

• 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: 4-(4-Hydroxyphenyl)semicarbazide
• 英文别名: 1-amino-3-(4-hydroxyphenyl)urea
• CAS: 73469-92-8
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: NTSXSCNGNVDTJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.4
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamino)acetic acid 、 4-(4-Hydroxyphenyl)semicarbazide 在 三氯氧磷 作用下， 以73%的产率得到4-[(5-[4-hydroxylphenylamino]-1,3,4-oxadiazol-2-yl)methylamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Discovery of novel antitubercular 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1,3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues

  摘要：

  In search of potential therapeutics for tuberculosis, we describe herewith the synthesis, characterization and antimycobacterial activity of 1,5-dimethyl-2-phenyl-4-([5-(arylamino)-1,3,4-oxadiazol-2-yl]methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues. Among the synthesized compounds, 4-1(5-1( 4-fluorophenylamino[-1,3,4-oxadiazol-2-yl)methylamino]-1,2-dihydro-1,5-dimethyl-2-Phenylpyrazol-3-one (4a) was found to be the most promising compound active against Mycobacterium tuberculosis H(37)Rv and isoniazid resistant M. tuberculosis with minimum inhibitory concentrations, 0.78 and 3.12 mu g/mL, respectively, free from any cytotoxicity (>62.5 mu g/mL). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.014
• 作为产物：
  描述：

  N(hydroxy-4 phenyl) carbamate de phenyle 在 hydrazine hydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以97%的产率得到4-(4-Hydroxyphenyl)semicarbazide
  参考文献：
  名称：

  通过氨基甲酸苯酯由相应的胺和肼制备取代的氨基脲

  摘要：

  开发了一种简单的合成方法，用于将胺和肼转化为取代的氨基脲。所需的胺和氯甲酸苯酯之间最初的缩合成氨基甲酸苯酯，然后在碱性条件下加入肼。该反应可耐受各种官能团，条件温和，收率高。

  DOI：

  10.1016/j.tetlet.2014.01.052

文献信息

• Preparation of substituted semicarbazides from corresponding amines and hydrazines via phenyl carbamates
  作者：Rebecca Hron、Branko S. Jursic

  DOI：10.1016/j.tetlet.2014.01.052

  日期：2014.2

  A simple synthetic procedure for the conversion of amines and hydrazines into substituted semicarbazides was developed. The initial condensation between the desired amine and phenyl chloroformate into phenyl carbamate is followed by the addition of hydrazine under basic conditions. The reaction is tolerable to a variety of functional groups, with mild conditions and high percent yields.

  开发了一种简单的合成方法，用于将胺和肼转化为取代的氨基脲。所需的胺和氯甲酸苯酯之间最初的缩合成氨基甲酸苯酯，然后在碱性条件下加入肼。该反应可耐受各种官能团，条件温和，收率高。
• Method of processing a silver halide color photographic material and a
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US05064751A1

  公开（公告）日：1991-11-12

  A method for processing a silver halide color photographic material including the step of developing the silver halide color photographic material with a color developing solution containing at least one aromatic primary amine developing agent and at least one hydrazide represented by the following formula (I) or (II) R.sup.1 --X.sup.1 --NHNH--R.sup.2 (I) in which X.sup.1 represents --CO--, --SO.sub.2 -- or ##STR1## R.sup.1 represents a hydroxyl group, a hydroxyamino group, carbamoyl group, a hydrazinocarbonyl group, an amino group, or a hydrazino group; and R.sup.2 represents a hydrogen atom, an alkyl group, or an aryl group; provided that the R.sup.1 or R.sup.2 groups of at least two of the hydrazide groups may be linked to form a dimer or higher polymer of the hydrazide. R.sup.3 --X.sup.2 --NHNH--R.sup.4 (II) in which X.sup.2 represents --CO-- or --SO.sub.2 --; R.sup.3 represents a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, or an aryloxy group; and R.sup.4 represents a hydrogen atom, an alkyl group or an aryl group; provided that the R.sup.3 or R.sup.4 groups of at least two of the hydrazide groups may be linked to form a dimer or higher polymer of the hydrazide. The method provides increased developer stability and reduced fog formation, particularly in continuous processing.

  一种处理银卤化物彩色照相材料的方法，包括以下步骤：用含有至少一种芳香族原始胺显影剂和至少一种由以下公式（I）或（II）表示的肼类化合物的显色显影溶液显影银卤化物彩色照相材料。其中，X1代表—CO—、—SO2—或##STR1##，R1代表羟基、羟基氨基、氨甲酰基、肼甲酰基、氨基或肼基；R2代表氢原子、烷基或芳基；但至少两个肼基的R1或R2基团可连接形成肼的二聚体或更高聚合物。R3—X2—NHNH—R4（II）其中，X2代表—CO—或—SO2—，R3代表氢原子、烷基、芳基、杂环基、烷氧基或芳氧基；R4代表氢原子、烷基或芳基；但至少两个肼基的R3或R4基团可连接形成肼的二聚体或更高聚合物。该方法提供了增加显影剂稳定性和减少雾化现象的效果，特别是在连续处理中。
• Kramer, Claus-Ruediger; Beck, Lothar, Zeitschrift fur Chemie, 1980, vol. 20, # 1, p. 25 - 26
  作者：Kramer, Claus-Ruediger、Beck, Lothar

  DOI：——

  日期：——
• [EN] INDAN-1,3-DIONE AND INDAN-1,2,3-TRIONE DERIVATIVES, PROCESSES FOR THE PREPARATION OF SAME AND THEIR APPLICATION AS THERAPEUTIC AGENTS<br/>[FR] DERIVES D'INDANE-1,3-DIONE ET D'INDANE-1,2,3-TRIONE, LEURS PROCEDES DE PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：INNOTHERA

  公开号：WO1993020045A1

  公开（公告）日：1993-10-14

  (EN) Compounds of formula (I) used as therapeutic agents. R2 and R3 are independently H, C1-C4 alkoxy or OH and (A, B) = (oxygen, oxygen) in which case either R or R1 is OH, halogen, secondary amino or tertiary amine while the other denotes NHNHCONHR4 or R and R1 together form =N-NH-CX-NHR5, =N-NH-CX-N(phenyl)2, =N-NH-CX-NH-NH-R5, =N-NH-C(SCH3)=N-R6 or =N-N=C(SCH3)-NH-R6; or (A, B) = (N-OH, oxygen) in which case R and R1 together form =N-NH-CX-NHR5 or =N-NH-CX-N(phenyl)2; or (A, B) = (N-NH-CX-NHR5, oxygen) in which case R and R1 together form =N-NH-CX-NHR5; or (A, B) = (N-OH, N-OH) in which case R and R1 together form =N-NH-CX-NHR5 or =N-NH-CX-N(phenyl)2.(FR) Composés utiles en thérapeutique de formule (I) dans laquelle R2 et R3 représentent indépendamment l'un de l'autre H, alkoxy en C1-C4 ou OH et (A, B) = (oxygène, oxygène), auquel cas l'un parmi R et R1 représente OH, halogène, amino secondaire ou amine tertiaire et l'autre représente NHNHCONHR4 ou bien R et R1 forment ensemble =N-NH-CX-NHR5, =N-NH-CX-N(phényle)2, =N-NH-CX-NH-NH-R5, =N-NH-C(SCH3)=N-R6 ou =N-N=C(SCH3)-NH-R6; ou (A, B) = (N-OH, oxygène), auquel cas R et R1 forment ensemble =N-NH-CX-NHR5 ou =N-NH-CX-N(phényle)2; ou (A, B) = (N-NH-CX-NHR5, oxygène), auquel cas R et R1 forment ensemble =N-NH-CX-NHR5; ou (A, B) = (N-OH, N-OH), auquel cas R et R1 forment ensemble =N-NH-CX-NHR5 ou =N-NH-CX-N(phényle)2.
• Synthesis of N-aryl and N-arylcarbamoylamino derivatives of 1,3-diazinane-5-carboxamide and their activity against glioblastoma LN-229 cell line
  作者：Rebecca J. Hron、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2016.09.074

  日期：2016.12

  Six structural motifs based on the initial (lead) structure of merbarone were designed, prepared, and tested against the glioblastoma LN-229 cell line. Three different structural moieties were modified in the search for optimal glioblastoma activity: the 1,3-diazinane moiety, the aryl moiety, and the heteroatom linker. Calculated molecular descriptors such as lipophilicity (ClogP), acidic strength (calculated pK(a)), and polar surface area (PSA) were used to design a diverse structural library of these compounds. From six different structural motifs and 136 compounds, a handful of examples with moderate (100 mu g/ml), good (10 mu g/ml) and excellent (1 mu g/ml) glioblastoma activity were elucidated. (C) 2016 Published by Elsevier Ltd.