1-phenyl-3-(nicotinoylamino)carbamide | 54809-91-5

• 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: 1-phenyl-3-(nicotinoylamino)carbamide
• 英文别名: 2-nicotinoyl-N-phenylhydrazinecarboxamide；1-nicotinoyl-4-phenyl-3-semicarbazide；1-nicotinoyl-4-phenyl semicarbazide；1-Nicotinoyl-4-phenyl-semicarbazid；3-[(2-phenylaminocarbonyl)hydrazinocarbonyl]pyridine；N-phenyl-2-(3-pyridinylcarbonyl)hydrazinecarboxamide；1-phenyl-3-(pyridine-3-carbonylamino)urea
• CAS: 54809-91-5
• 化学式: C₁₃H₁₂N₄O₂
• 分子量: 256.264
• InChiKey: XYKAUCVQKPRTFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  247 °C
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(nicotinoylamino)carbamide 在 sodium 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 9.5h， 生成 N-phenyl-2-(4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-ylthio)acetamide
  参考文献：
  名称：

  Khatale, Pravin N.; Sivakumar; Mahajan, Niranjan S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 890 - 899

  摘要：

  DOI：
• 作为产物：
  描述：

  烟酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-phenyl-3-(nicotinoylamino)carbamide
  参考文献：
  名称：

  Khatale, Pravin N.; Sivakumar; Mahajan, Niranjan S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 890 - 899

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
  作者：Oleksandr Grytsai、Oksana Valiashko、Manon Penco-Campillo、Maeva Dufies、Anais Hagege、Luc Demange、Sonia Martial、Gilles Pagès、Cyril Ronco、Rachid Benhida

  DOI：10.1016/j.bioorg.2020.104271

  日期：2020.11

  Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect

  合成了携带3-氨基-1,2,4-三唑支架的两个系列的化合物，并使用XTT分析评估了它们对一组癌细胞系的抗癌活性。重新讨论了第一批吡啶基衍生物的1,2,4-三唑合成。生物学结果表明，对于这两个系列，不能替代的3-氨基-1,2,4-三唑核的有效性以及在三唑的3位的3-溴苯基氨基部分具有明显的有益作用（化合物2.6和4.6）在多个测试的细胞系上。此外，我们的结果指出了这些化合物的抗血管生成活性。总体而言，5-芳基-3-苯基氨基-1,2,4-三唑结构具有有前途的双重抗癌活性。
• SYNTHESIS OF SUBSTITUTED 1,3,4-THIADIAZOLES USING LAWESSON'S REAGENT
  作者：B. Gierczyk、M. Zalas

  DOI：10.1080/00304940509354950

  日期：2005.6

  oxychloride or sulfuric acid have been used in such reactions. Another route for 1,3,4-thiadiazole ring synthesis, is via exchange of the oxygen atom in 1,3,4-oxadiazole to sulfur, using tetraphosphorus decasulfide or thiourea;I2 however in our experience, this method does not work in many cases. Lawesson has described the thionation of 1 ,2-diacylhydrazineswith 2,4bis(4-methoxypheny1)1,2,3,4-dithiadiphosphetane

  含硫化合物具有许多特殊和独特的性质，这使它们继续受到关注。由于其广泛的生物活性谱，1,3,4-噻二唑已被检查为潜在的抗菌剂，“抗病毒？镇痛剂：抗肿瘤剂：抗惊厥药、消炎药～、药物、杀虫剂和杀菌剂。其中一些形成热致液晶并具有有趣的电光特性。6 此外，噻二唑已被用作腐蚀和氧化抑制剂^,^染料或金属离子络合剂~。~ ~ J ~ J 这类化合物最常用的合成方法包括硫酰肼或其他底物与 SCNNCS 部分的环化和脱水。'2,6 通常在此类反应中使用磷酰氯或硫酸。1,3,4-噻二唑环合成的另一种途径是通过将 1,3,4-恶二唑中的氧原子交换为硫，使用十硫化四磷或硫脲；I2 但是根据我们的经验，这种方法在许多情况下不起作用案件。Lawesson 描述了 1 ,2-二酰基肼与 2,4 双(4-甲氧基苯基)1,2,3,4-二噻二膦（劳森试剂）的硫化作用，然后是自发环化和脱氢硫化，这是一种改进的噻二唑环形成方法。
• Novel compounds for the management of aging-related and diabetic vascular complications, process for their preparation, therapeutic and cosmetic uses thereof
  申请人：TORRENT PHARMACEUTICALS LTD.

  公开号：US20030045554A1

  公开（公告）日：2003-03-06

  The invention discloses a new clause of a five membered heterocylic ring compounds of general formula 1 1 and its pharmaceutically or cosmetically acceptable salts, wherein R1, R2, R3, R4, R5, A, B, X and Y are as defined in the specification. The invention also discloses a process for preparation of these compound and their therapeutic and cosmetic applications particularly in the management of aging related and diabetic vascular complications. The compounds in question act by triple action of an AGE (Advanced Glycation Endproducts) breaker, AGE inhibitor and free radical scavenger which make them most suitable in different therapeutic and cosmetic applications. The invention also discloses pharmaceuticals and cosmetic compositions comprising these compounds and method of treatment of diseases caused by accumulation of AGE and/or free radicals in the body cells.

  本发明公开了一种新的通式11的五元杂环化合物及其药学或美容学可接受的盐，其中R1、R2、R3、R4、R5、A、B、X和Y在说明书中定义。本发明还公开了制备这些化合物及其治疗和美容应用的方法，特别是在管理与衰老相关和糖尿病血管并发症方面。所述化合物通过AGE（高级糖基化终产物）断裂剂、AGE抑制剂和自由基清除剂的三重作用发挥作用，使它们在不同的治疗和美容应用中最为适用。本发明还公开了包含这些化合物的药物和化妆品组合物以及治疗由体细胞中AGE和/或自由基积累引起的疾病的方法。
• Composition and method for use of pyridinium derivatives in cosmetic and therapeutic applications
  申请人：Torrent Pharmaceuticals Ltd

  公开号：EP1304101A1

  公开（公告）日：2003-04-23

  The invention discloses a new class of compounds particularly pyridinium derivatives, which have been found to exhibit triple function of a free radical scavenger (antioxidant), AGE breaker and AGE inhibitor, and cosmetic composition comprising these compounds contained in a cosmetically acceptable carrier. The invention also discloses a method of cosmetic application by applying such composition. The invention further discloses a pharmaceutical composition, comprising said compounds useful in scavenging free radicals from the body cells of a mammal, a method of scavenging free radicals from the body cells of a mammal and a method of treating of diseases caused by accumulation of free radicals in the body cells of a mammal by administering a composition made with the compounds of the invention. The invention in addition, also discloses composition and method for inhibiting AGE in a mammal by use of the compounds of the same group.

  本发明公开了一类新化合物，特别是吡啶鎓衍生物，它们被发现具有自由基清除剂（抗氧化剂）、AGE 破坏剂和 AGE 抑制剂的三重功能，还公开了包含在化妆品可接受载体中的这些化合物的化妆品组合物。本发明还公开了一种通过施用此类组合物进行美容的方法。本发明进一步公开了一种药物组合物，其中包含有助于清除哺乳动物体细胞中自由基的所述化合物；一种清除哺乳动物体细胞中自由基的方法；以及一种通过施用用本发明化合物制成的组合物治疗哺乳动物体细胞中自由基积累引起的疾病的方法。此外，本发明还公开了通过使用同组化合物抑制哺乳动物体内 AGE 的组合物和方法。
• Novel compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof
  申请人：TORRENT PHARMACEUTICALS LTD.

  公开号：US20030032660A1

  公开（公告）日：2003-02-13

  Novel compounds of the pyridinium series useful for the management of diabetes and aging-related vascular and neurovascular complications, including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory disorders, immunological disorders, oxidative stress, dermatological disorders and discoloration of teeth, by breaking preformed AGE, of the general formula I, or pharmaceutically acceptable salts thereof, 1 wherein, R 1 , R 2 , R 3 , X and m are as defined in the specification. Also disclosed is a method for preparation of the compounds of general formula (I) and pharmaceutical composition containing one or more compounds as defined above as active ingredients. Also disclosed is a method of treatment of a diabetic patient by administering the compounds as defined above, either singly or in combination with drugs for antidiabetic therapy.

  吡啶系列新型化合物，通过破坏通式 I 的预形成 AGE 或其药学上可接受的盐，用于治疗糖尿病和与衰老相关的血管和神经血管并发症，包括肾病、神经损伤、动脉粥样硬化、视网膜病变、炎症性疾病、免疫学疾病、氧化应激、皮肤病和牙齿变色、 1 其中，R 1 , R 2 , R 3 X和m如说明书中所定义。还公开了通式（I）化合物的制备方法和含有一种或多种如上定义的化合物作为活性成分的药物组合物。还公开了一种治疗糖尿病患者的方法，通过单独施用或与抗糖尿病治疗药物联合施用上述定义的化合物。