(4-nitro-benzyl)-urea | 18740-35-7

• 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-nitro-benzyl)-urea
• 英文别名: (4-Nitro-benzyl)-harnstoff；[(4-Nitrophenyl)methyl]urea；(4-nitrophenyl)methylurea
• CAS: 18740-35-7
• 化学式: C₈H₉N₃O₃
• mdl: MFCD13195911
• 分子量: 195.178
• InChiKey: JTVLKCKOMVXJQH-UHFFFAOYSA-N

物化性质

• 熔点：
  206-207 °C(Solv: ethanol (64-17-5))
• 沸点：
  393.6±34.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-nitro-benzyl)-urea 在 sodium methylate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 79.5h， 生成 (2-(1-(4-methoxybenzyl)-5-(4-nitrobenzyl)-1,4,5,6-tetrahydro-4,6-dioxo-1,3,5-triazin-2-ylamino)ethyl)guanidine
  参考文献：
  名称：

  A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists

  摘要：

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.030
• 作为产物：
  描述：

  N'-(p-Methoxybenzyl)-N-hydroxyguanidine hydrochloride 在 phosphate buffer 、 水 、 溶剂黄146 、 sodium nitrite 作用下， 反应 0.33h， 生成 (4-nitro-benzyl)-urea
  参考文献：
  名称：

  N-Nitrosated N-hydroxyguanidines are nitric oxide-releasing diazeniumdiolates

  摘要：

  N-Hydroxyguanidines 可被亚硝基转化为具有晶体学确认结构 H2N+C[NHR][N(O)NO]- 的齐聚二氮杂环戊酸酯，其在生理 pH 值下的水解解离可产生 NO 和 N2O；这些结果似乎解释了将 NG-羟基-L-精氨酸（哺乳动物 NO 生物合成过程中的代谢中间产物）暴露于有氧 NO 时产生的 "潜在细胞间一氧化氮载体 "的形成原因。

  DOI：

  10.1039/a801543k

文献信息

• PHENYL DERIVATIVES AND THEIR USE AS A MEDICAMENT
  申请人：Poitout Lydie

  公开号：US20100056507A1

  公开（公告）日：2010-03-04

  The present invention relates to new phenylic derivatives exhibiting a good affinity for certain sub-types of cannabinoid receptors, in particular the CB2 receptors. These derivatives are of particular interest in a method for treating pathological conditions and diseases in which one or more cannabinoid receptors are involved. The invention also relates to pharmaceutical compositions containing said new phenylic derivatives and to methods for the preparation and use thereof.

  本发明涉及新的苯基衍生物，具有良好的亲和力，特别是对CB2受体的某些亚型。这些衍生物在治疗涉及一个或多个大麻素受体的病理条件和疾病的方法中具有特殊的兴趣。本发明还涉及含有这些新的苯基衍生物的药物组合物，以及其制备和使用方法。
• 8-Quinolinxanthine and 8-isoquinolinxanthine derivatives as pde 5 inhibitors
  申请人：——

  公开号：US20030171384A1

  公开（公告）日：2003-09-11

  A compound of formula (I) in free or salt form, where R 1 is hydrogen or alkyl optionally substituted by hydroxy, alkoxy, or alkylthio, R 2 is hydrogen, alkyl, hydroxyalkyl, alkylcarbonyloxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, cycloalkylalkyl, heterocyclylalkyl, aralkyl in which the aryl ring thereof is optionally fused to a 5-membered heterocyclic group or is optionally substituted by one or more substituents selected from alkoxy, amino, alkylamino, dialkylamino, acylamino, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfonylamino or dialkylaminosulfonylamino, R 3 is hydrogen or alkyl optionally substituted by hydroxy, alkoxy, or alkylthio, R 4 is hydrogen or alkyl, R 5 is a quinolinyl, isoquinolinyl or oxodihydroisoquinolinyl group optionally fused to a 5-membered heterocyclic group and optionally substituted by one or more substituents selected from halogen, cyano, hydroxy, alkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkenyl, alkoxycarbonyl, alkynyl, carboxyl, acyl, a group of formula —N(R 6 )R 7 , aryl optionally substituted by one or more substituents selected from halogen or alkoxy, or heteroaryl having 5 or 6 ring atoms attached through a ring carbon atom to the indicated carbon atom, and R 6 and R 7 are each independently hydrogen or alkyl optionally substituted by hydroxy or alkoxy or one of R 6 and R 7 is hydrogen and the other is acyl, or R 6 and R 7 together with the nitrogen atom to which they are attached denote a 5- or 6-membered heterocyclyl group.

  化合物的结构式(I)在自由或盐形式下，其中R1为氢或烷基，可以选择地被羟基、烷氧基或烷硫基取代，R2为氢、烷基、羟基烷基、烷基羰基氧基烷基、烷氧基烷基、烷硫基烷基、烯基、环烷基烷基、杂环烷基烷基、芳基烷基，其中芳环可以选择地与一个5-成员杂环基团融合，或可以选择地被烷氧基、氨基、烷基氨基、二烷基氨基、酰胺基、卤素、羟基、氨基磺酰基、烷基氨基磺酰基、二烷基氨基磺酰基、烷基磺酰氨基或二烷基氨基磺酰氨基等一个或多个取代基取代，R3为氢或烷基，可以选择地被羟基、烷氧基或烷硫基取代，R4为氢或烷基，R5为喹啉基、异喹啉基或氧代二氢异喹啉基，可以选择地与一个5-成员杂环基团融合，并可以选择地被卤素、氰基、羟基、烷基、羟基烷基、烷氧基烷基、烷硫基烷基、烷氧基、烷硫基、烯基、烷氧羰基、炔基、羧基、酰基、一个结构式为—N(R6)R7的基团、可以选择地被卤素或烷氧基等一个或多个取代基取代的芳基，或者通过一个环碳原子连接到所指示的碳原子的5个或6个环原子的杂芳基，R6和R7分别独立地为氢或烷基，可以选择地被羟基或烷氧基取代，或者R6和R7中的一个为氢，另一个为酰基，或者R6和R7与它们连接的氮原子一起表示一个5-或6-成员杂环基团。
• Combinations
  申请人：——

  公开号：US20030114469A1

  公开（公告）日：2003-06-19

  The present invention relates to a pharmaceutical composition, comprising (a) a phosphodiesterase 5 inhibitor or a pharmaceutically acceptable salt thereof and (b) at least one of the active ingredients selected from the group consisting of (i) an anti-diabetic agent; (ii) HMG-Co-A reductase inhibitors; (iii) an anti-hypertensive agent; and (iv) a serotonin reuptake inhibitor (SSRI) or, in each case, or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier. The pharmaceutical composition may be employed for the treatment of sexual dysfunction, hyperglycemia, hyperinsulinaemia, hyperlipidaemia, hypertriglyceridemia, diabetes, insulin resistance, impaired glucose metabolism, conditions of impaired glucose tolerance (IGT), conditions of impaired fasting plasma glucose, obesity, diabetic retinopathy, diabetic nephropathy, glomerulosclerosis, diabetic neuropathy, syndrome X, erectile dysfunction, coronary heart disease, hypertension, especially ISH, angina pectoris, myocardial infarction, stroke, vascular restenosis, endothelial dysfunction, impaired vascular compliance, congestive heart failure.

  本发明涉及一种药物组合物，包括(a) 磷酸二酯酶5抑制剂或其药用盐，以及(b) 来自以下组中选择的至少一种活性成分(i) 抗糖尿病药物；(ii) HMG-Co-A还原酶抑制剂；(iii) 抗高血压药物；和(iv) 血清素再摄取抑制剂（SSRI）或在每种情况下，其药用盐；以及药学上可接受的载体。该药物组合物可用于治疗性功能障碍、高血糖、高胰岛素血症、高脂血症、高甘油三酯血症、糖尿病、胰岛素抵抗、糖代谢受损、糖耐量受损（IGT）病状、空腹血糖受损病状、肥胖、糖尿病视网膜病、糖尿病肾病、肾小球硬化、糖尿病神经病变、X综合征、勃起功能障碍、冠心病、高血压，尤其是高收缩压高血压（ISH），心绞痛、心肌梗死、中风、血管再狭窄、内皮功能障碍、血管顺应性受损、充血性心力衰竭。
• [EN] CHROMAN DERIVATIVES<br/>[FR] DERIVES DE CHROMANE
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：WO1998004542A1

  公开（公告）日：1998-02-05

  (EN) The present invention relates to chroman derivatives of formula (I): wherein R1 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C1-6 alkoxy group, a C3-6 alkoxymethyl group, etc.; R3 and R4 each independently represent a hydrogen atom, a C1-6 alkyl group, etc.; R5 represents a hydroxyl group or a C1-6 alkylcarbonyloxyl group or forms a bond together with R5; R6 represents a hydrogen atom or forms a bond together with R5; R7 and R8 each independently represent a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a phenyl group, etc.; n is 0 or an integer of 1, 2, 3, or 4; W represents a phenyl group, etc.; X represents C=O, CH2, SO2, etc.; Y represents NR17 (in which R17 represents a hydrogen atom, a C1-4 alkyl group, a phenyl group, etc.), etc.; Z does not exist or represents CH2 or NR18 (R18 represents a hydrogen atom, a C1-4 alkyl group, or a phenyl group, etc.) or their salts.(FR) La présente invention concerne des dérivés de chromane de la formule (I) ou leurs sels. Dans ladite formule (I), R1 représente un atome d'halogène, un goupe alkyle C1-6, un groupe alkoxy C1-6, un groupe alkoxyméthyle C3-6 etc.; R3 et R4 représentent chacun, indépendamment, un atome dhydrogène, un groupe alkyle C1-6, etc; R5 représente un groupe hydroxyle ou un groupe alkylcarbonyloxyle C1-6 ou forme une liaison avec R5; R6 représente un atome d'hydrogène ou forme une liaison avec R5; R7 et R8 représentent chacun, indépendamment, un atome d'hydrogène, un groupe alkyle C1-6, un groupe cycloalkyle C3-6, un groupe phényle, etc.; n est égal à 0 ou est un entier de 1, 2, 3, ou 4; W représente un groupe phényle etc.; X représente C=O, CH2, SO2, etc.; Y représente NR17 (R17 représentant un atome d'hydrogène, un groupe alkyle C1-4, un groupe phényle, etc.), etc.; Z n'existe pas ou représente CH2 ou NR18 (R18 représentant un atome d'hydrogène, un groupe alkyle C1-4, ou un groupe phényle, etc.).

  本发明涉及公式（I）的色甘醇衍生物，其中R1代表氢原子，卤原子，C1-6烷基，C1-6烷氧基，C3-6烷氧甲基等；R3和R4各自独立地代表氢原子，C1-6烷基等；R5代表羟基或C1-6烷基羰氧基基团，或与R5一起形成键；R6代表氢原子或与R5一起形成键；R7和R8各自独立地代表氢原子，C1-6烷基，C3-6环烷基，苯基等；n为0或1,2,3或4的整数；W代表苯基等；X代表C=O，CH2，SO2等；Y代表NR17（其中R17代表氢原子，C1-4烷基，苯基等）等；Z不存在或代表CH2或NR18（其中R18代表氢原子，C1-4烷基或苯基等）或它们的盐。
• 8-Quinolinxanthine and 8-isoquinolinxanthine derivatives as PDE 5 inhibitors
  申请人：Bhalay Gurdip

  公开号：US20060106214A1

  公开（公告）日：2006-05-18

  A compound of formula (I) R 1 is hydrogen or alkyl optionally substituted by hydroxy, alkoxy, or alkylthio, R 2 is hydrogen, alkyl, hydroxyalkyl, alkylcarbonyloxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, cycloalkylalkyl, heterocyclylalkyl, aralkyl in which the aryl ring thereof is optionally fused to a 5-membered heterocyclic group or is optionally substituted by one or more substituents selected from alkoxy, amino, alkylamino, dialkylamino, acylamino, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsufonylamino or dialkylaminosulfonylamino, R 3 is hydrogen or alkyl optionally substituted by hydroxy, alkoxy, or alkylthio, R 4 is hydrogen or alkyl, R 5 is a quinolinyl, isoquinolinyl or oxodihydroisoquinolinyl group optionally fused to a 5-membered heterocyclic group and optionally substituted by one or more substituents selected from halogen, cyano, hydroxy, alkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkenyl, alkoxycarbonyl, alkynyl, carboxyl, acyl, a group of formula —N(R 6 )R 7 , aryl optionally substituted by one or more substituents selected from halogen or alkoxy, or heteroaryl having 5 or 6 ring atoms attached through a ring carbon atom to the indicated carbon atom, and R 6 and R 7 are each independently hydrogen or alkyl optionally substituted by hydroxy or alkoxy or one of R 6 and R 7 is hydrogen and the other is acyl, or R 6 and R 7 together with the nitrogen atom to which they are attached denote a 5- or 6- membered heterocyclyl group.

  化合物的式子（I）中，R1是氢或烷基，可以选择性地被羟基、烷氧基或烷基硫代取代，R2是氢、烷基、羟基烷基、烷基羧酸酯基、烷氧基烷基、烷基硫代烷基、烯基、环烷基烷基、杂环烷基烷基、芳基烷基，其中芳环可以选择性地与5元杂环基融合或可以选择性地被一种或多种取代基所取代，这些取代基包括烷氧基、氨基、烷基氨基、二烷基氨基、酰胺基、卤素、羟基、氨基磺酰基、烷基氨基磺酰基、二烷基氨基磺酰基、烷基磺酰氨基或二烷基氨基磺酰氨基，R3是氢或烷基，可以选择性地被羟基、烷氧基或烷基硫代取代，R4是氢或烷基，R5是喹啉基、异喹啉基或氧代二氢异喹啉基，可以选择性地与5元杂环基融合并可以选择性地被一种或多种取代基所取代，这些取代基包括卤素、氰基、羟基、烷基、羟基烷基、烷氧基烷基、烷基硫代烷基、烷氧基、烷基硫代基、烯基、烷氧羰基、炔基、羧基、酰基、式子-N（R6）R7的基团、芳基，其中芳基可以选择性地被一种或多种取代基所取代，这些取代基包括卤素或烷氧基，或者是通过一个环碳原子与所指定的碳原子相连的含有5个或6个环原子的杂环芳基，R6和R7各自独立地是氢或烷基，可以选择性地被羟基或烷氧基取代，或者R6和R7中的一个是氢，另一个是酰基，或者R6和R7连同它们所附着的氮原子一起表示一个含有5个或6个环原子的杂环基团。