1-(3-氨基丙基)-3-苯基脲 | 7509-94-6

• 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-(3-氨基丙基)-3-苯基脲
• 英文名称: N-(3-Aminopropyl)-N'-phenylurea
• 英文别名: 1-(3-aminopropyl)-3-phenylurea
• CAS: 7509-94-6
• 化学式: C₁₀H₁₅N₃O
• 分子量: 193.249
• InChiKey: CBYQZENFYCTUIA-UHFFFAOYSA-N

物化性质

• 沸点：
  320.4±34.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 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：
  67.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙氧基苯甲醛 、 1-(3-氨基丙基)-3-苯基脲 在 sodium methylate 、 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 1-[3-[(3-Ethoxyphenyl)methylamino]propyl]-3-phenylurea
  参考文献：
  名称：

  Urea-Based Inhibitors of Trypanosoma brucei Methionyl-tRNA Synthetase: Selectivity and in Vivo Characterization

  摘要：

  Urea-based methionyl-tRNA synthetase inhibitors were designed, synthesized, and evaluated for their potential toward treating human African trypanosomiasis (HAT). With the aid of a homology model and a structure activity-relationship approach, low nM inhibitors were discovered that show high selectivity toward the parasite enzyme over the closest human homologue. These compounds inhibit parasite growth with EC50 values as low as 0.15 mu M while having low toxicity to mammalian cells. Two compounds (2 and 26) showed excellent membrane permeation in the MDR1-MDCKII model and encouraging oral pharmacokinetic properties in mice. Compound 2 was confirmed to enter the CNS in mice. Compound 26 had modest suppressive activity against Trpanosoma brucei rhodesiense in the mouse model, suggesting that more potent analogues or compounds with higher exposures need to be developed. The urea-based inhibitors are thus a promising starting point for further optimization toward the discovery of orally available and CNS active drugs to treat HAT.

  DOI：

  10.1021/jm300303e
• 作为产物：
  描述：

  异氰酸苯酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(3-氨基丙基)-3-苯基脲
  参考文献：
  名称：

  Urea-Based Inhibitors of Trypanosoma brucei Methionyl-tRNA Synthetase: Selectivity and in Vivo Characterization

  摘要：

  Urea-based methionyl-tRNA synthetase inhibitors were designed, synthesized, and evaluated for their potential toward treating human African trypanosomiasis (HAT). With the aid of a homology model and a structure activity-relationship approach, low nM inhibitors were discovered that show high selectivity toward the parasite enzyme over the closest human homologue. These compounds inhibit parasite growth with EC50 values as low as 0.15 mu M while having low toxicity to mammalian cells. Two compounds (2 and 26) showed excellent membrane permeation in the MDR1-MDCKII model and encouraging oral pharmacokinetic properties in mice. Compound 2 was confirmed to enter the CNS in mice. Compound 26 had modest suppressive activity against Trpanosoma brucei rhodesiense in the mouse model, suggesting that more potent analogues or compounds with higher exposures need to be developed. The urea-based inhibitors are thus a promising starting point for further optimization toward the discovery of orally available and CNS active drugs to treat HAT.

  DOI：

  10.1021/jm300303e

文献信息

• Design, synthesis and biological evaluation of dehydroabietic acid derivative as potent vasodilatory agents
  作者：Dan Wu、Xiaoting Li、Qing-Kun Shen、Run-Hui Zhang、Qian Xu、Xiao-Tong Sang、Xing Huang、Chang-Hao Zhang、Zhe-Shan Quan、Li-Hua Cao

  DOI：10.1016/j.bioorg.2022.106110

  日期：2022.12

  Using dehydroabietic acid as the lead compound for structural modification, 25 dehydroabietic acid derivatives were synthesized. Among them, compound D1 not only showed the strongest relaxation effect on the aortic vascular ring in vitro (Emax = 99.5 ± 2.1%, EC50 = 3.03 ± 0.96 µM), but also significantly reduced systolic and diastolic blood pressure in rats at a dose of 2.0 mg/kg in vivo. Next, the

  以脱氢松香酸为先导化合物进行结构修饰，合成了25种脱氢松香酸衍生物。其中，化合物D1不仅在体外对主动脉血管环表现出最强的舒张作用（Emax=99.5±2.1%，EC 50 =3.03±0.96μM），而且在一定剂量下能显着降低大鼠的收缩压和舒张压。体内浓度为 2.0 mg/kg。接下来，通过HUVECs进一步研究最佳活性D1的血管保护作用及其分子机制。结果表明， D1以浓度依赖性方式诱导大鼠胸主动脉内皮依赖性舒张。使用 NG -硝基-l-精氨酸甲酯 ( l -NAME)、1 H -[1,2,4]-恶二唑并-[4,3-a]-喹喔啉-1-酮 (ODQ) 去除内皮或主动脉环预处理）和四乙铵（TEA）显着抑制D1诱导的松弛。此外，渥曼青霉素、KT5823、曲西立宾、地尔硫卓、BaCl 2 、4-氨基吡啶、吲哚美辛、普萘洛尔和阿托品可减弱D1诱导的血管舒张作用。 D1增加了 HUVEC 中 eNOS
• Wasserlösliche faserreaktive Phthalocyaninverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0075905A2

  公开（公告）日：1983-04-06

  Wasserlösliche faserreaktive Phthalocyaninverbindungen der allgemeinen Formel (1) in welcher Pc den Rest des metallfreien oder metallhaltigen Phthalocyanins, bedeutet, wobei die Sulfonsäure- bzw. Sulfonamidgruppen in den 3-Stellungen der aromatischen Ringe des Phthalocyanins gebunden sind, R, und R2 jeweils ein Wasserstoffatom oder eine Alkylgruppe von 1-6 Kohlenstoffatomen, die durch Methoxy-, Äthoxy-, Propoxy-, C2H5-O-C2H4-0-, Cyano-, Acetylamino-, Carboxy-, HO3S-, H203P-, Phenyl-, Methylphenyl-, Methoxyphenyl-, Dimethylamino, Diäthylamino-, ß-Hydroxyäthylamino-, β-Hydroxyäthoxy-, N-Phenylureido-, N-Alkylc, c, ureido- oder N-Cycloalkylureidogruppen substituiert sein kann, oder eine Allyl-, 2-Methallyl-, Crotyl- oder Cycloalkylgruppe bedeuten, und R, und R2 zusammen mit dem Stickstoffatom den Rest eines heterocyclischen gesättigten oder ungesättigten Rings darstellen können, oder R, und R2 einen Phenylrest, der durch Methyl-, Äthyl-, Methoxy-, Äthoxy-, Carboxy- oder Sulfonsäuregruppen substituiert sein kann, darstellen, R3 ein Wasserstoffatom oder eine Alkylgruppe von 1 bis 4 Kohlenstoffatomen, welche durch Hydroxy- oder Carboxygruppen substituiert sein kann, bedeutet, X ein Wasserstoffatom oder eine Alkyl- oder Alkoxygruppe von 1 bis 4 Kohlenstoffatomen darstellt, Y die Vinylgruppe oder die Gruppierung der Formel -CH2-CH2-Z darstellt, in welcher Z einen anorganischen oder organischen alkalisch eliminierbaren Rest bedeutet, a eine Zahl zwischen 0 und 2, b eine Zahl zwischen 0 und 2 und c eine Zahl zwischen, 1,7 und 2.6 darstellen, mit der Maßgabe, daß die Summe aus a, b und c höchstens 4 ist, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Wolle, Seide, Polyamidfasern, Leder oder hydroxygruppenhaltigen Materialien.

  通式（1）的水溶性纤维活性酞菁化合物 其中 Pc 表示无金属或含金属酞菁的基团，磺酸或磺酰胺基团键合在酞菁芳香环的 3 位，Rß-羟乙基氨基、β-羟乙基氧基、N-苯基脲基、N-烷基c、c、脲基或 N-环烷基脲基，或烯丙基、2-甲基烯丙基、丁基或环烷基，R 和 R2 连同氮原子可代表饱和或不饱和杂环的基团、或 R 和 R2 代表可被甲基、乙基、甲氧基、乙氧基、羧基或磺酸基取代的苯基， R3 代表氢原子或可被羟基或羧基取代的 1 至 4 个碳原子的烷基、X 代表氢原子或 1 至 4 个碳原子的烷基或烷氧基，Y 代表乙烯基或式-CH2-CH2-Z 的基团，其中 Z 代表无机或有机碱基，a 代表 0 至 2 之间的数字，b 代表 0 至 2 之间的数字，c 代表 1.7 至 2 之间的数字。6，但 a、b 和 c 之和最多为 4，其制备方法及其用于羊毛、丝绸、聚酰胺纤维、皮革或含有羟基的材料染色的用途。
• US4576755A
  申请人：——

  公开号：US4576755A

  公开（公告）日：1986-03-18
• US8524894B2
  申请人：——

  公开号：US8524894B2

  公开（公告）日：2013-09-03
• Urea-Based Inhibitors of Trypanosoma brucei Methionyl-tRNA Synthetase: Selectivity and in Vivo Characterization
  作者：Sayaka Shibata、J. Robert Gillespie、Ranae M. Ranade、Cho Yeow Koh、Jessica E. Kim、Joy U. Laydbak、Frank H. Zucker、Wim G. J. Hol、Christophe L. M. J. Verlinde、Frederick S. Buckner、Erkang Fan

  DOI：10.1021/jm300303e

  日期：2012.7.26

  Urea-based methionyl-tRNA synthetase inhibitors were designed, synthesized, and evaluated for their potential toward treating human African trypanosomiasis (HAT). With the aid of a homology model and a structure activity-relationship approach, low nM inhibitors were discovered that show high selectivity toward the parasite enzyme over the closest human homologue. These compounds inhibit parasite growth with EC50 values as low as 0.15 mu M while having low toxicity to mammalian cells. Two compounds (2 and 26) showed excellent membrane permeation in the MDR1-MDCKII model and encouraging oral pharmacokinetic properties in mice. Compound 2 was confirmed to enter the CNS in mice. Compound 26 had modest suppressive activity against Trpanosoma brucei rhodesiense in the mouse model, suggesting that more potent analogues or compounds with higher exposures need to be developed. The urea-based inhibitors are thus a promising starting point for further optimization toward the discovery of orally available and CNS active drugs to treat HAT.