4-(4-phenyl-1H-imidazol-1-yl)butan-1-amine | 173838-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-phenyl-1H-imidazol-1-yl)butan-1-amine
• 英文别名: 4-phenyl-1H-imidazole-1-butanamine；4-(4-phenyl-imidazol-1-yl)butylamine；4-(4-phenylimidazol-1-yl)butan-1-amine
• CAS: 173838-41-0
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: UQCVEQOKBOJPNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-9-methoxy-5,7,9,11,13-pentamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester 、 4-(4-phenyl-1H-imidazol-1-yl)butan-1-amine 以 乙腈 为溶剂， 反应 40.0h， 生成 benzoic acid 4-dimethylamino-2-{4-ethyl-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxo-1-[4-(4-phenyl-imidazol-1-yl)-butyl]-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of C12 des-methyl ketolides

  摘要：

  Synthesis of C-12 des-methyl ketolide is developed featuring an intramolecular epoxide formation/elimination process to establish the C-12 stereocenter. These ketolides are potent against several key respiratory pathogens, including erythromycin resistant erm- and mef-containing strains of Streptococcus pneumoniae. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.104
• 作为产物：
  描述：

  4-苯基咪唑 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-phenyl-1H-imidazol-1-yl)butan-1-amine
  参考文献：
  名称：

  Synthesis and antibacterial activity of HMR 3647 a new ketolide highly potent against erythromycin-resistant and susceptible pathogens

  摘要：

  In the search for new ketolides with improved activities against erythromycin-resistant S. pneumoniae and H. influenzae we synthesized a new 11,12 carbamate ketolide substituted by an imidazo-pyridyl side chain: HMR 3647. This compound demonstrated a potent activity against erythromycin susceptible and resistant pathogens, including penicillin G/erythromycin A-resistant S. pneumoniae and H. influenzae. In vivo, HMR 3647 displayed good pharmacokinetic parameters (Cmax = 2.9 mu g/ml, bioavailability = 49%, AUC(0-8) = 17.2 mu g.h/l, t(1/2) = 1h) and was shown to have a high therapeutic efficacy in mice infected by various respiratory pathogens, including multi-resistant S. pneumoniae and Gram negative bacteria such as H. influenzae. HMR 3647 appears to be a very promising agent for the treatment of respiratory infections and is currently in clinical trials. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00534-x

文献信息

• C12 Modified erythromycin macrolides and ketolides having antibacterial activity
  申请人：——

  公开号：US20030125266A1

  公开（公告）日：2003-07-03

  Antimicrobial macrolide compounds are provided having formulas II: 1 as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有II:1式的抗微生物大环内酯化合物，以及其药用盐、酯或前药；包含这类化合物的药物组合物；通过给予这类化合物治疗细菌感染的方法；以及这类化合物的制备方法。
• Synthesis and antibacterial activity of novel C12 ethyl ketolides
  作者：Matthew T. Burger、Christy Hiebert、Mehran Seid、Daniel T. Chu、Lynn Barker、Mike Langhorne、Ribhi Shawar、Jolene Kidney、Manoj C. Desai、Jacob J. Plattner

  DOI：10.1016/j.bmc.2006.04.032

  日期：2006.8

  A novel series of C(12) ethyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens, including those resistant to erythromycin. The C(12) modification involves replacing the natural C(12) methyl group in the erythromycin core with an ethyl group via chemical synthesis. From the C(12) ethyl macrolide core, a series of C(12) ethyl ketolides

  已经发现了一系列新的C（12）乙基红霉素衍生物，它们对关键的呼吸道病原体（包括对红霉素有抗性的病原体）表现出体外和体内效力。C（12）修改涉及通过化学合成用乙基取代红霉素核心中的天然C（12）甲基。从C（12）乙基大环内酯核心制备了一系列C（12）乙基酮缩酮，并测试了其对一组相关临床分离株的抗菌活性。无论是由于核糖体甲基化（erm）还是外排（mef），都发现了几种对大环内酯类敏感和耐药菌有效的化合物。特别是，C（12）乙基酮缩酮4k，4s，4q，4m和4t具有相似的抗菌谱，并且具有与商业酮内酯telithromycin相当的活性。
• Pyridyl substituted ketolide antibiotics
  申请人：Burger T. Matthew

  公开号：US20050009764A1

  公开（公告）日：2005-01-13

  Antimicrobial macrolide and ketolide compounds are provided having formulas XII: as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.

  提供具有XII式的抗微生物大环内酯和酮内酯化合物，以及其药学上可接受的盐、酯或前药；包含这些化合物的药物组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• [EN] PYRIDYL SUBSTITUTED KETOLIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES A BASE DE KETOLIDE A SUBSTITUTION PYRIDYLE
  申请人：CHIRON CORP

  公开号：WO2004096822A3

  公开（公告）日：2004-12-16
• Synthesis and antibacterial activity of a novel series of acylides active against community acquired respiratory pathogens
  作者：Rajesh Kumar、Sujata Rathy、Atul K. Hajare、Yogesh B. Surase、Jyoti Dullu、Jitendra S. Jadhav、R. Venkataramanan、Anjan Chakrabarti、Manisha Pandya、Pragya Bhateja、G. Ramkumar、Biswajit Das

  DOI：10.1016/j.bmcl.2011.10.101

  日期：2012.1

  A novel series of acylides 4 were designed to overcome antibacterial resistance and evaluated for in vitro and in vivo activity. This series of acylides was designed from clarithromycin by changing the substitution on the desosamine nitrogen, followed by conversion to 3-O-acyl and 11,12-carbamate. These compounds showed significantly potent antibacterial activity against not only Gram-positive pathogens, including macrolide-lincosamide-streptogramin B (MLSB)-resistant and efflux-resistant strains, but also Gram-negative pathogens such as Haemophilus influenzae. These acylides also showed better activity against telithromycin resistant Streptococcus pneumoniae strains. (C) 2011 Elsevier Ltd. All rights reserved.