1-(4-氨基咪唑并[4,5-c]喹啉-1-基)-2-甲基丙烷-2-醇 | 112668-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-(4-氨基咪唑并[4,5-c]喹啉-1-基)-2-甲基丙烷-2-醇
• 英文名称: 1-(4-aminoimidazo [4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
• 英文别名: 4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline；1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine；4-amino-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；1-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol；4-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol；1-(4-aminoimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
• CAS: 112668-45-8
• 化学式: C₁₄H₁₆N₄O
• 分子量: 256.307
• InChiKey: CNBOKXFMODKQCT-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-氨基咪唑并[4,5-c]喹啉-1-基)-2-甲基丙烷-2-醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-amino-8-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
  参考文献：
  名称：

  WO2006/91394

  摘要：

  公开号：
• 作为产物：
  描述：

  1-[(3-氨基-2-氯-4-喹啉)氨基]-2-甲基-2-丙醇 在 氨 作用下， 以 甲苯 为溶剂， 生成 1-(4-氨基咪唑并[4,5-c]喹啉-1-基)-2-甲基丙烷-2-醇
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v

文献信息

• [EN] 4-AMINO-IMIDAZOQUINOLINE COMPOUNDS<br/>[FR] COMPOSÉS DE 4-AMINO-IMIDAZOQUINOLINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015162075A1

  公开（公告）日：2015-10-29

  This invention relates to novel 4-amino-imidazoquinoline compounds of the formula (I) wherein R1 to R4 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer or infectious diseases.

  这项发明涉及公式（I）中的新型4-氨基咪唑喹啉化合物，其中R1至R4如描述和索赔中定义，并且其药学上可接受的盐。这些化合物是TLR激动剂，因此可能作为治疗癌症或传染病等疾病的药物而有用。
• 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
  申请人：Riker Laboratories, Inc.

  公开号：US04689338A1

  公开（公告）日：1987-08-25

  1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described.

  1H-咪唑并[4,5-c]喹啉-4-胺是抗病毒药物。还描述了使用这些化合物的药理学方法以及含有这些化合物的药物组合物。
• [EN] COMPOUNDS AND METHODS TO INCREASE ANTI-P-GLYCOPROTEIN ACTIVITY OF BAICALEIN BY ALKYLATION ON THE A RING<br/>[FR] COMPOSES ET METHODES DESTINEES A AUGMENTER L'ACTIVITE ANTI-GLYCOPROTEINE P PAR ALKYLATION SUR LE NOYAU A
  申请人：UNIV YALE

  公开号：WO2005075449A1

  公开（公告）日：2005-08-18

  The present invention is directed to analogs of baicalein according to formula (I): where R5 is H, (CI-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl group, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate or phosphodiester group; R6 and R7 are each independently H, (C1-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl or together form a -OCR1R20- group wherein each of R1 and R2 is independently H, a C1-C3 alkyl group or an optionally substituted phenyl or benzyl group; and R8 is H, OH, an O-acyl group, a C1,-C4 alkyl or alkoxy group, F, Cl, Br or I, or a pharmaceutically acceptable salt thereof, which exhibit anti-P-glycoprotein activity and methods of enhancing the bioavailability of active compounds, especially orally administered compounds, by inhibition of P-glycoprotein 170 (P-gp 170) and/or CYP450 enzyme, especially CYP450 3A4 enzyme. Pharmaceutical compositions based upon these novel derivatives according to the present invention are also described herein.

  本发明涉及根据式(I)的黄芩素类似物：其中R5为H，(C1-C12)烷基，(C2-C13)酰基，或者一个可选择取代的苯基或苄基团，酰基，C1-C20烷基或醚基，磷酸酯，二磷酸酯，三磷酸酯或磷酸二酯基团；R6和R7各自独立地为H，(C1-C12)烷基，(C2-C13)酰基，或者一个可选择取代的苯基或苄基，或者一起形成一个-OCR1R20-基团，其中R1和R2中的每一个独立地为H，C1-C3烷基或可选择取代的苯基或苄基团；以及R8为H，OH，一个O-酰基团，一个C1-C4烷基或烷氧基团，F，Cl，Br或I，或其药学上可接受的盐，具有抗P-糖蛋白活性，并通过抑制P-糖蛋白170 (P-gp 170)和/或CYP450酶，特别是CYP450 3A4酶，来增强活性化合物的生物利用度的方法。根据本发明的这些新颖衍生物基础上的药物组合物也在此描述。
• Delivery of immune response modifier compounds using metal-containing particulate support materials
  申请人：3M Innovative Properties Company

  公开号：US20040202720A1

  公开（公告）日：2004-10-14

  The present invention provides immune response modifiers (IRMs) on particulate support materials that includes one or more metals, including alloys or complexes thereof.

  本发明提供了一种包括一种或多种金属（包括合金或配合物）的颗粒支持材料上的免疫应答调节剂（IRM）。
• Delivery of immune response modifier compounds
  申请人：——

  公开号：US20040258698A1

  公开（公告）日：2004-12-23

  The present invention provides immune response modifiers (IRMs) associated with (typically, attached to, and preferably, covalently attached to) macromolecular support materials. The IRM compounds in such IRM-support complexes retain biological activity. Such attachment of an IRM to a macromolecular support material provides for the localized biological activity of the IRM.

  本发明提供了与（通常与、最好是共价连接到）大分子支持材料相关联的免疫应答调节剂（IRM）。这种IRM-支持复合物中的IRM化合物保留生物活性。将IRM连接到大分子支持材料上，实现了IRM的局部生物活性。