1-(2-羟乙基)-3-(4-甲氧基苯基)脲 | 87919-18-4

• 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: 1-(2-羟乙基)-3-(4-甲氧基苯基)脲
• 英文名称: 1-(2-hydroxyethyl)-3-(4-methoxyphenyl)urea
• 英文别名: Urea, N-(2-hydroxyethyl)-N'-(4-methoxyphenyl)-
• CAS: 87919-18-4
• 化学式: C₁₀H₁₄N₂O₃
• mdl: MFCD00452749
• 分子量: 210.233
• InChiKey: DTSMZZIGSBXWAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-羟乙基)-3-(4-甲氧基苯基)脲 在 哌啶乙酸盐 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 1-(2-{4-[2,4-Dioxo-thiazolidin-(5Z)-ylidenemethyl]-phenoxy}-ethyl)-3-(4-methoxy-phenyl)-urea
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  甲氧苯胺 在 吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 1-(2-羟乙基)-3-(4-甲氧基苯基)脲
  参考文献：
  名称：

  Synthesis and evaluation in vitro of 1-[2-(10-dihydroartemisininoxy) ethyl]-3-phenylurea derivatives as potential agents against cancer

  摘要：

  In order to develop potent and selective anticancer agents, a series of novel artemisinin derivatives bearing urea moiety 1a-n were facilely synthesized herein and screened for their activities in vitro against ten human tumor cell lines (HeLa, MCF-7, U937, K562, HL60, HCT116, HepG2, A549, A375-S2, and HT1080). The pharmacological results indicated that some compounds showed excellent activity against cancer cell lines and good selectivity, especially the compound 1c which proved to be the most active against the cancer cells as well as distinctive patterns of selectivity.

  DOI：

  10.1007/s00044-012-0319-0

文献信息

• A Convenient Method of Synthesis of Unsymmetrical Urea Derivatives
  作者：Grażyna Groszek

  DOI：10.1021/op020055g

  日期：2002.11.1

  A method for the preparation of unsymmetrical urea derivatives that may contain functional groups such as hydroxyl, amine, amide, and carboxyl is described. The method consists of a one-pot modified Curtius rearrangement starting with appropriate aromatic acid chloride and carried out in a nonaqueous system

  描述了一种制备可能含有羟基、胺、酰胺和羧基等官能团的不对称脲衍生物的方法。该方法包括一锅改进的 Curtius 重排，从适当的芳族酰氯开始，并在非水系统中进行
• Investigation of the Mitsunobu Reaction of<i>N</i>-(2-Hydroxyethyl)-<i>N′</i>-Phenyl-Ureas
  作者：Taek Hyeon Kim、Gue-Jae Lee、Mi-Hyun Cha

  DOI：10.1080/00397919908086441

  日期：1999.8

  The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN=NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.
• [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents
  作者：Barrie C. C. Cantello、Michael A. Cawthorne、Graham P. Cottam、Peter T. Duff、David Haigh、Richard M. Hindley、Carolyn A. Lister、Stephen A. Smith、Peter L. Thurlby

  DOI：10.1021/jm00049a017

  日期：1994.11

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.
• Synthesis and evaluation in vitro of 1-[2-(10-dihydroartemisininoxy) ethyl]-3-phenylurea derivatives as potential agents against cancer
  作者：Wei Luo、Ming-yu Xia、Takashi Ikejima、Li-hua Li、Chun Guo

  DOI：10.1007/s00044-012-0319-0

  日期：2013.7

  In order to develop potent and selective anticancer agents, a series of novel artemisinin derivatives bearing urea moiety 1a-n were facilely synthesized herein and screened for their activities in vitro against ten human tumor cell lines (HeLa, MCF-7, U937, K562, HL60, HCT116, HepG2, A549, A375-S2, and HT1080). The pharmacological results indicated that some compounds showed excellent activity against cancer cell lines and good selectivity, especially the compound 1c which proved to be the most active against the cancer cells as well as distinctive patterns of selectivity.