(4-硝基苯基)尿素 | 556-10-5

• 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: (4-硝基苯基)尿素
• 中文别名: 1-(4-硝基苯基)脲
• 英文名称: p-nitrophenylurea
• 英文别名: N-(4-nitrophenyl)urea；p-Nitrophenylharnstoff；(4-Nitro-phenyl)-harnstoff；(4-nitrophenyl)urea；1-(4-nitrophenyl)urea
• CAS: 556-10-5
• 化学式: C₇H₇N₃O₃
• mdl: MFCD09040599
• 分子量: 181.151
• InChiKey: LXXTVGKSGJADFU-UHFFFAOYSA-N

物化性质

• 熔点：
  150℃
• 沸点：
  314.24°C (rough estimate)
• 密度：
  1.490
• 溶解度：
  溶于甲醇、乙醇、二甲基甲酰胺
• 最大波长(λmax)：
  327nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (4-硝基苯基)尿素 在 tributyl phosphate-NO₂ 作用下， 以 various solvent(s) 为溶剂， 以93%的产率得到p-nitrobenzene diazonium nitrate
  参考文献：
  名称：

  Zhang, Z.; Liu, X.; Zhang, Q., Organic Preparations and Procedures International, 2001, vol. 33, # 3, p. 305 - 310

  摘要：

  DOI：
• 作为产物：
  描述：

  p-nitrophenyl carbamoyl chloride 在 ammonium hydroxide 作用下， 生成 (4-硝基苯基)尿素
  参考文献：
  名称：

  Grammaticakis,P., Bulletin de la Societe Chimique de France, 1967, p. 84 - 94

  摘要：

  DOI：

文献信息

• Dimethylformamide Catalyzed Synthesis of Novel Heterocycles-Their Characterization and Antimicrobial Evaluation
  作者：Vijay V. Dabholkar、Sunil R. Patil、Rajesh V. Pandey

  DOI：10.1002/jhet.1073

  日期：2013.3

  Indandione 1 was brominated to yield 2‐bromoIndandione 2, which further reacted with substituted thiocarbamides, carbamides, 2‐aminothiophenols, 2‐aminophenol, and triazole to furnished 3‐substituted aniline‐2‐thia‐4‐aza‐6,7‐benzo‐8‐oxo‐bicyclo[3.3.0]‐1(5),3‐octadiene 3, 3‐substituted aniline‐2‐oxa‐4‐aza‐6,7‐benzo‐8‐oxo‐bicyclo[3.3.0]‐1(5),3‐octadiene 4, 2‐Thia‐5‐aza‐9‐oxo‐3,4‐(3′‐substituted) benzo‐7

  茚满二酮1溴化生成2-溴茚满二酮2，后者进一步与取代的硫代氨基甲酸酯，脲，2-氨基硫酚，2-氨基苯酚和三唑反应生成3取代的苯胺-2-二硫杂-4-氮杂-6,7-苯并呋喃。 -8-氧代双环[3.3.0] -1（5），3-辛二烯3，3-取代的苯胺-2-氧杂-4-氮杂-6,7-苯并-8-氧代-双环[3.3.0 ] -1（5），3-辛二烯4，2 -Thia-5-氮杂-9-oxo-3,4-（3'-取代）苯并-7,8-苯并双环[4.3.0] -1 （6）壬烯5，2-氧杂-5-氮杂-9-氧代（3,4） - （7,8） -二苯并-二环[4.3.0] -1（6）壬烯6，3'-取代-（1'，2'，4'）triazolo [5,6-b] [indeno（2,3-e）]-1,3,4-噻二嗪7， 分别。根据光谱技术阐明了化合物的结构，进一步筛选了具有代表性的化合物的抗菌活性。
• [EN] COMPOUNDS FOR THE MODULATION OF CYCLOPHILINS FUNCTION<br/>[FR] COMPOSÉS POUR LA MODULATION DE LA FONCTION DES CYCLOPHILINES
  申请人：UNIV COURT UNIV OF EDINBURGH

  公开号：WO2020043831A1

  公开（公告）日：2020-03-05

  The present invention relates to compounds of formula (I) or a pharmaceutically acceptable salt thereof useful as inhibitors of Cyclophilins and modulators of cyclophilin-like proteins. The invention also relates to uses of said compounds in the treatment of various disorders. Formula (I), wherein: R1 and R2 are each independently is selected from the group consisting of -R, -haloalkyl, -hydroxyalkyl, -OR, -C(O)R, -CO2R, -C(O)N(R)2, -NRC(O)R, and - N(R)2; wherein R2 could also be a sulphide; each R is independently hydrogen, C 1-6 aliphatic, C3-10 aryl, a 3-8 membered saturated or partially unsaturated carbocyclic ring, a 3-7 membered heterocylic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, sulphur, or a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms selected from nitrogen, oxygen, or sulphur; R3 is Formual (Ia) selected from the group consisting of -OEt, and wherein R5 and R6 are independently selected from the group consisting of H, halide, methoxy, thiomethyl, morpholine and trifluoromethyl;R4 is selected from the group consisting of C1-6-alkyl-, and R4.1-CH2- wherein, R4.1 is C3-6-cycloalkyl-, a 5-6 membered heterocyclic ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, sulphur; optionally substituted with one R4.1.1 wherein, R4.1.1 is selected from -H, C1-4-alkyl, optionally substituted with one substituent selected from H2N(O)C- or EtO(O)C-;X is carbon or nitrogen; A is selected from the group consisting of 6 membered unsaturated ring, with 1-3 nitrogen atoms, which is optionally substituted by -NH2,and Formula (Ib), wherein ring B is a fused 5-10 membered saturated or partially unsaturated heterocyclic mono- bicyclic ring having 1-3 heteroatoms selected from nitrogen, oxygen or sulphur, which is optionally substituted by -OH; and m is 1 or 2; and n is 1 or 2.

  本发明涉及式(I)的化合物或其药学上可接受的盐，其作为环肽酶的抑制剂和环肽酶样蛋白的调节剂。该发明还涉及所述化合物在治疗各种疾病中的用途。式(I)中：R1和R2各自独立地选自由-R、-卤代烷基、-羟基烷基、-OR、-C(O)R、-CO2R、-C(O)N(R)2、-NRC(O)R和-N(R)2等组成的群；其中R2也可以是硫化物；每个R独立地是氢、C1-6脂肪基、C3-10芳基、一个3-8成员饱和或部分不饱和的碳环、一个具有1-4个异原子（从氮、氧、硫中独立选择）的3-7成员杂环、或一个具有1-4个异原子（从氮、氧、硫中选择）的5-6成员单环杂芳基；R3是式(Ia)中选自-OEt的群，其中R5和R6各自独立地选自H、卤素、甲氧基、硫甲基、吗啉和三氟甲基的群；R4选自C1-6-烷基-和R4.1-CH2-，其中，R4.1是C3-6环烷基-、一个具有1-4个异原子（从氮、氧、硫中独立选择）的5-6成员杂环，可选地用一个R4.1.1取代，其中R4.1.1选自-H、C1-4-烷基，可选地用一个取代基（从H2N(O)C-或EtO(O)C-中选择）取代；X是碳或氮；A选自具有1-3个氮原子的6成员不饱和环，可选地用-NH2取代；和式(Ib)，其中环B是一个融合的5-10成员饱和或部分不饱和的杂环单双环，具有1-3个从氮、氧或硫中选择的异原子，可选地用-OH取代；m为1或2；n为1或2。
• Synthesis and Evaluation of Novel 4-Substituted Styryl Quinazolines as Potential Antimicrobial Agents
  作者：Rahul P. Modh、Amit C. Patel、Dharmesh H. Mahajan、Christophe Pannecouque、Erik De Clercq、Kishor H. Chikhalia

  DOI：10.1002/ardp.201200291

  日期：2012.12

  antibacterial and anti‐human immunodeficiency virus (HIV) agents, a series of 22 novel styryl quinazoline‐based heterocyclic entities were designed and synthesized. Various substituted aryl urea and thiourea cores were incorporated at position 4 of quinazoline, followed by styrylation of position 2, aiming at an augmented biological potential. The synthesized compounds were well characterized through

  为了提供可能的抗菌和抗人类免疫缺陷病毒 (HIV) 试剂，设计并合成了一系列 22 种新型苯乙烯基喹唑啉基杂环实体。各种取代的芳基脲和硫脲核被掺入喹唑啉的 4 位，然后是 2 位的苯乙烯基化，旨在增强生物潜力。合成的化合物通过IR、1H NMR、13C NMR和元素分析得到了很好的表征。筛选了所有化合物对 HIV-1 (IIIB) 和 HIV-2 (ROD) 毒株的体外抗 HIV 活性。还评估了对各种致病性革兰氏阳性和革兰氏阴性细菌菌株的抗菌活性。
• Design and Synthesis of Novel N-(4-(Pyridin-2-yloxy)benzylidene)-4- [4-(substituted)phenyl]semicarbazides as Potential Anticonvulsant Agents
  作者：Prem Singh、Laxmi Tripathi

  DOI：10.14233/ajchem.2018.21368

  日期：——

  A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.

  考虑到药效团结构的必要性，设计并合成了新的N-(4-(吡啶-2-氧基)苯亚甲基)-4-[4-(取代)苯基]氨基脲系列化合物(PSSD1-8)，并评估了它们的潜在抗惊厥活性。所有衍生物均按所给方案合成，反应过程通过薄层色谱监测。通过FT-IR、1H NMR、质谱和元素分析确认了合成衍生物的结构。在MES和scMET惊厥模型中通过腹腔注射给药后，确认了它们的抗惊厥活性。系列中最活跃的化合物是1-(4-(吡啶-2-氧基)苯亚甲基)-4-对甲苯基氨基脲(PSSD5)。通过分子对接研究评估了与目标受体/酶的相互作用和结合模式。这些化合物被发现与人类γ-氨基丁酸受体(GABAAR-β3)紧密结合。还进行了计算研究，以预测合成化合物的药代动力学特性。
• One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
  作者：Tun-Cheng Chien、Chien-Hong Wang、Tsung-Han Hsieh、Chia-Chi Lin、Wen-Hsiung Yeh、Chih-An Lin

  DOI：10.1055/s-0034-1381007

  日期：——

  Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot

  由腈与羟胺反应获得的酰胺肟，在苯磺酰氯（TsCl 或 o-NsCl）存在下进行 Tiemann 重排，形成 N-取代的氰胺。随后，氰胺酸水解得到相应的 N-单取代脲。从腈合成 N-单取代脲是通过三步一锅完成的，这提供了从各种腈中直接获得多功能 N-单取代脲衍生物的途径。