1-trityl-2-aminoimidazole | 185563-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-trityl-2-aminoimidazole
• 英文别名: 2-amino-1-(triphenylmethyl)imidazole；1-triphenylmethyl-2-aminoimidazole；1-(triphenylmethyl)imidazole-2-ylamine；N-trityl-2-aminoimidazole；1-trityl-1H-imidazole-2-amine；2-amino-1-tritylimidazole；2-Amino-1-trityl-imidazole；1-tritylimidazol-2-amine
• CAS: 185563-93-3
• 化学式: C₂₂H₁₉N₃
• 分子量: 325.413
• InChiKey: HKYAKZXAOGNRHX-UHFFFAOYSA-N

物化性质

• 沸点：
  546.6±60.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1-trityl-2-aminoimidazole 在 lithium hydroxide 、 三乙酰氧基硼氢化钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.5h， 生成 (S)-2-(3,5-Dimethyl-biphenyl-4-sulfonylamino)-3-({5-[4-(1-trityl-1H-imidazol-2-ylamino)-butyl]-4,5-dihydro-isoxazole-3-carbonyl}-amino)-propionic acid
  参考文献：
  名称：

  Isoxazolines as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  Starting with lead compound 2, we sought to increase the selectivity for alpha(v)beta(3)-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent alpha to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of alpha(v)beta(3). In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for alpha(v)beta(3)-mediated adhesion versus alpha(IIb)beta(3)-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the alpha-substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective alpha(v)beta(3) antagonist 3h was found to be a potent inhibitor of alpha(v)beta(3)-mediated cell migration.

  DOI：

  10.1021/jm9900321
• 作为产物：
  描述：

  1Triphenylmethyl-2-phthalimidoimidazole 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到1-trityl-2-aminoimidazole
  参考文献：
  名称：

  Isoxazolines as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  Starting with lead compound 2, we sought to increase the selectivity for alpha(v)beta(3)-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent alpha to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of alpha(v)beta(3). In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for alpha(v)beta(3)-mediated adhesion versus alpha(IIb)beta(3)-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the alpha-substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective alpha(v)beta(3) antagonist 3h was found to be a potent inhibitor of alpha(v)beta(3)-mediated cell migration.

  DOI：

  10.1021/jm9900321
• 作为试剂：
  描述：

  1-Trityl-2-[(dimethylamino)methylene]aminoimidazole 、 乙醇 、 肼 在 crude product 、 二氯甲烷 、 sodium hydroxide 、 Brine 、 Sodium sulfate-III 、 1-trityl-2-aminoimidazole 作用下， 以 溶剂黄146 为溶剂， 反应 5.25h， 以to obtain 1-trityl-2-aminoimidazole, 4 (37.2 g, 97%)的产率得到1-trityl-2-aminoimidazole
  参考文献：
  名称：

  Linkers for anchoring targeting ligands

  摘要：

  一种改进的连接剂，其在疏水锚点和靶向剂之间缺乏手性中心，适用于体内使用，具有适当的疏水/亲水性能，可用于与基于脂质的粒子进行耦合。

  公开号：

  US07998462B2

文献信息

• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Weinstein David S.

  公开号：US20090075995A1

  公开（公告）日：2009-03-19

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity, including inflammatory and immune diseases, having the structure of formula (I): an enantiomer, diastereomer, or tautomer thereof, or a prodrug ester thereof, or a pharmaceutically-acceptable salt thereof, in which: Z is heterocyclo or heteroaryl; A is a 5- to 8-membered carbocyclic ring or a 5- to 8-membered heterocyclic ring; B is a cycloalkyl, cycloalkenyl, aryl, heterocyclo, or heteroaryl ring, wherein each ring is fused to the A ring on adjacent atoms and optionally substituted by one to four groups which are the same or different and are independently selected from R 5 , R 6 , R 7 , and R 8 ; J 1 , J 2 , and J 3 are at each occurrence the same or different and are independently -A 1 QA 2 -; Q is a bond, O, S, S(O), or S(O) 2 ; A 1 and A 2 are the same or different and are at each occurrence independently selected from a bond, C 1-3 alkylene, substituted C 1-3 alkylene, C 2-4 alkenylene, and substituted C 2-4 alkenylene, provided that A 1 and A 2 are chosen so that ring A is a 5- to 8-membered carbocyclic or heterocyclic ring; R 1 to R 11 are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一系列新颖的非甾体化合物，这些化合物在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中很有用，包括炎性和免疫疾病，具有以下结构式（I）： 其对应的光学异构体、对映异构体或互变异构体，或其前药酯，或其药用可接受盐，其中： Z是杂环或杂芳基； A是一个5至8成员的碳环或一个5至8成员的杂环； B是一个环烷基、环烯基、芳基、杂环或杂芳基环，其中每个环都与A环上的相邻原子融合，并且可以选择性地被一个到四个独立选自R5、R6、R7和R8的相同或不同的组取代； J1、J2和J3每次出现时相同或不同，独立地选自-A1QA2-；Q是键、O、S、S(O)或S(O)2；A1和A2相同或不同，每次出现时独立地选自键、C1-3烷基、取代的C1-3烷基、C2-4烯基和取代的C2-4烯基，前提是A1和A2的选择使得环A是一个5至8成员的碳环或杂环； R1至R11如本文所述定义。 还提供了使用这些化合物的药物组合物和治疗炎性疾病、免疫相关疾病、肥胖和糖尿病的方法。
• Integrin receptor antagonists
  申请人：The DuPont Merck Pharmaceutical Company

  公开号：US05710159A1

  公开（公告）日：1998-01-20

  This invention relates to novel heterocycle compounds including but not limited to 3-\x9b3-\x9b3-(imidazolin-2-yl amino)propyloxy!isoxazol-5-ylcarbonylamino!-2-(benzyloxycarbonylamino)-pro pionic acid, which are useful as antagonists of the .alpha..sub.v .beta..sub.3 and related integrin receptors, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of cell adhesion and the treatment of angiogenic disorders, inflammation, bone degradation, tumors, metastases, thrombosis, and other cell aggregation-related conditions.

  这项发明涉及新型杂环化合物，包括但不限于3-（咪唑啉-2-基氨基）丙氧基异噁唑-5-基甲酰氨基-2-（苄氧羰基氨基）丙酸，这些化合物可用作αvβ3及相关整合素受体的拮抗剂，以及含有这些化合物的药物组合物、制备这些化合物的方法，以及使用这些化合物单独或与其他治疗剂联合用于抑制细胞粘附和治疗血管生成障碍、炎症、骨质破坏、肿瘤、转移、血栓形成和其他细胞聚集相关疾病的方法。
• [EN] PRO-SURVIVAL COMPOUNDS<br/>[FR] COMPOSÉS FAVORISANT LA SURVIE
  申请人：UNIV GLASGOW

  公开号：WO2016092327A1

  公开（公告）日：2016-06-16

  Disclosed herein are a class of compounds useful in cell culture, in particular, the in vitro culture of stem cells. The compounds have been found to promote the survival and/or maintenance of stem cells in (or during) culture and/or throughout passage.

  本文披露了一类在细胞培养中有用的化合物，特别是体外培养干细胞。已发现这些化合物能促进干细胞在培养过程中的存活和/或维持，并/或在传代过程中。
• SIMULTANEOUS IMAGING OF CARDIAC PERFUSION AND A VITRONECTIN RECEPTOR TARGETED IMAGING AGENT
  申请人：——

  公开号：US20040208823A1

  公开（公告）日：2004-10-21

  The present invention describes a method of concurrent imaging in a mammal comprising: a) administering to said mammal a vitronectin receptor targeted imaging agent and a perfusion imaging agent; and b) concurrently detecting the vitronectin receptor targeted imaging agent bound at the vitronectin receptor and the perfusion imaging agent; and c) forming an image from the detection of said vitronectin targeted imaging agent and said perfusion imaging agent.

  本发明描述了一种哺乳动物的并行成像方法，包括：a)向该哺乳动物注射一个定向于血管紧张素受体的成像剂和一个灌注成像剂；并b)同时检测定向于血管紧张素受体的成像剂在血管紧张素受体上的结合和灌注成像剂；并c)从检测到的血管紧张素受体定向成像剂和灌注成像剂形成图像。
• [EN] ISOXAZOLINE AND ISOXAZOLE DERIVATIVES AS INTEGRIN RECEPTOR ANTAGONISTS<br/>[FR] DERIVES D'ISOXAZOLINE ET D'ISOXADOLE UTILISES COMME ANTAGONISTES DES RECEPTEURS DE L'INTEGRINE
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1996037492A1

  公开（公告）日：1996-11-28

  (EN) This invention relates to novel heterocycle compounds including but not limited to 3-[3-[3-(imidazolin-2-yl amino)propyloxy]isoxazol-5-ylcarbonylamino]-2-(benzyloxycarbonylamino)-propionic acid, which are useful as antagonists of the $g(a)v$g(b)3 and related integrin receptors, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of cell adhesion and the treatment of angiogenic disorders, inflammation, bone degradation, tumors, metastases, thrombosis, and other cell aggregation-related conditions.(FR) Cette invention se rapporte à de nouveaux composés hétérocycliques comprenant notamment, mais pas exclusivement, l'acide 3-[3-[3-(imidazoline-2-yl- amino)propyloxy]isoxasol-5-ylcarbonylamino]-2-(benzyloxycarbonylamino)-propionique et qui sont utilisés comme antagonistes des récepteurs $g(a)v$g(b)b3 et de l'intégrine apparentée. L'invention se rapporte également aux compositions pharmaceutiques contenant ces composés, aux procédés de préparation et d'utilisation de ces composés, seuls ou associés à d'autres agents thérapeutiques et destinés à être utilisés dans des procédés d'inhibition de l'adhésion cellulaire et de traitement de troubles angiogéniques, des inflammations, de la déperdition osseuse, des tumeurs, des métastases, de la thrombose et d'autres états apparentés à l'agrégation cellulaire.

  本发明涉及新型杂环化合物，包括但不限于3-[3-[3-(咪唑啉-2-基氨基)丙氧基]异噁唑-5-基甲酰胺]-2-(苄氧羰基氨基)丙酸，其作为$g(a)v$g(b)3和相关整合素受体的拮抗剂，以及含有这种化合物的制药组合物、制备这种化合物的过程，以及使用这些化合物的方法，单独或与其他治疗剂联合使用，用于抑制细胞黏附和治疗血管生成障碍、炎症、骨质破坏、肿瘤、转移、血栓形成和其他与细胞聚集相关的疾病。