2-[6,8-二氯-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-基]-N,N-二丙基乙酰胺 | 193979-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-[6,8-二氯-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-基]-N,N-二丙基乙酰胺
• 中文别名: 1-甲基-3-(丙-1-烯-2-基)环己烯
• 英文名称: CB 34
• 英文别名: N,N-di-n-propyl-[2-(4-chlorophenyl)-6,8-dichloroimidazo[1,2-a]pyridin-3-yl]acetamide；2-[6,8-dichloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylacetamide
• CAS: 193979-75-8
• 化学式: C₂₁H₂₂Cl₃N₃O
• 分子量: 438.784
• InChiKey: QYVWBXJKZUCSNI-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO：26 mg/mL，可溶

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  2-[6,8-二氯-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-基]-N,N-二丙基乙酰胺 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以96%的产率得到2-[6,8-Dichloro-2-(4-chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-N,N-dipropyl-propionamide
  参考文献：
  名称：

  Structure−Activity Relationships and Effects on Neuroactive Steroid Synthesis in a Series of 2-Phenylimidazo[1,2-a]pyridineacetamide Peripheral Benzodiazepine Receptors Ligands

  摘要：

  A series of 36 imidazopyridineacetamides (2-37) were designed and synthesized to evaluate the effects of structural changes on the amide nitrogen at both central (CBRs) and peripheral benzodiazepine receptors (PBRs). These changes include variations in the length and number of the alkyl groups as well as introduction of different aromatic, heteroaromatic, and conformationally constrained groups. The affinities of these compounds for CBRs and PBRs were determined, and the results indicate that bulkiness of the substituents, their branching, and length beyond an optimal value may cause hindrance to the ligand in its interaction with the receptor. The presence of aromatic or conformationally constrained substituents on the carboxamide nitrogen can be conducive to high affinity and selectivity. Furthermore, the ability of a subset of the most active ligands to stimulate synthesis of neuroactive steroids in plasma and brain was evaluated in vivo and in vitro. Compound 3 exhibited very marked effects on the peripheral and central synthesis of neuroactive steroids, while 36 (potent at subnanomolar level) showed a slight ability to affect neuroactive steroid content in the cerebral cortex.

  DOI：

  10.1021/jm049610q
• 作为产物：
  描述：

  4-(4-氯-苯基)-4-氧代-丁酸乙酯 在 sodium hydroxide 、 氯化亚砜 、 溴 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 3.0h， 生成 2-[6,8-二氯-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-基]-N,N-二丙基乙酰胺
  参考文献：
  名称：

  2-苯基咪唑并[1,2-α]吡啶衍生物的合成及其对中心和外围苯并二氮杂receptor受体的结合亲和力。针对外围类型的一系列新的高亲和力和选择性配体。

  摘要：

  若干个6-取代或6,8-二取代的2-苯基咪唑并[1,2-α-吡啶-3-羧酸烷基酯5a-h，-乙酸酯5i-s，6a-g和-丙酸酯5t，6h和N，N-二烷基-2-苯基咪唑并[1,2-α吡啶-3-甲酰胺7a-d，-乙酰胺7e-t或-丙酰胺7u是按照新的合成方法制备的，并且它们对两个环的亲和力（CBR ）和外围（PBR）苯并二氮杂receptor受体进行了评估。酯系列化合物对两种受体类型均显示出低亲和力。相反，大多数N，N-二烷基（2-苯基咪唑并[1,2-α吡啶基-3-基]乙酰胺）7e-t对CBR或PBR具有高亲和性和选择性，这取决于C（C 6）-和/或杂环系统上的C（8）。特别是，6-取代的化合物7f-n的IC50值之比（IC50（CBR）/ IC50（PBR））为0.32（7m）至232（7k），而6,8-二取代的化合物7o-t大于PBR的选择性是CBR的1000倍。检查了几种不同的苯二氮卓类

  DOI：

  10.1021/jm970112+

文献信息

• Hydrogel Prodrugs
  申请人：ASCENDIS PHARMA A/S

  公开号：US20150258205A1

  公开（公告）日：2015-09-17

  The present invention relates to a process for the preparation of a hydrogel and to a hydrogel obtainable by said process. The present invention further relates to a process for the preparation of a hydrogel-spacer conjugate, to a hydrogel-spacer conjugate obtainable by said process, to a process for the preparation of a carrier-linked prodrug and to carrier-linked prodrugs obtainable by said process, in particular to carrier-linked prodrugs that provide for a controlled or sustained release of a drug from a carrier. In addition, the invention relates to the use of the hydrogel for the preparation of a carrier-linked prodrug.

  本发明涉及一种制备水凝胶的方法，以及通过该方法可获得的水凝胶。本发明还涉及一种制备水凝胶-间隔物共轭物的方法，以及通过该方法可获得的水凝胶-间隔物共轭物，还涉及一种制备载体连结的前药的方法，以及通过该方法可获得的载体连结的前药，特别是提供了能够从载体中控制或持续释放药物的载体连结的前药。此外，本发明涉及使用水凝胶制备载体连结的前药。
• [EN] PROTECTING GROUP COMPRISING A PURIFICATION TAG<br/>[FR] GROUPE PROTECTEUR COMPRENANT UNE ÉTIQUETTE DE PURIFICATION
  申请人：ASCENDIS PHARMA AS

  公开号：WO2015052155A1

  公开（公告）日：2015-04-16

  The present invention relates to compounds comprising a protecting group moiety-tag moiety conjugate, a method of purification and monoconjugates obtained from such method of purification.

  本发明涉及包含保护基团-标记基团共轭物的化合物，以及一种纯化方法和从该纯化方法获得的单共轭物。
• Biodegradable Polyethylene Glycol Based Water-Insoluble Hydrogels
  申请人：Rau Harald

  公开号：US20120156259A1

  公开（公告）日：2012-06-21

  The present invention relates to biodegradable polyethylene glycol based water-insoluble hydrogels comprising backbone moieties which are interconnected by hydrolytically degradable bonds, the backbone moieties further comprising reactive functional groups, wherein the water-insoluble hydrogel is further characterized in that the ratio between the time period for the complete degradation of the hydrogel by hydrolysis of the degradable bonds into water-soluble degradation products comprising one or more backbone moieties and the time period for the release of the first 10 mol-% of water-soluble degradation products comprising one or more backbone moieties based on the total amount of backbone moieties in the hydrogel is greater than 1 and equal to or less than 2. The invention further relates to conjugates of such hydrogels with ligands or ligating groups, prodrugs and pharmaceutical compositions as well as their use in a medicament.

  本发明涉及可生物降解的聚乙二醇基水不溶性水凝胶，其包含通过水解降解键相互连接的骨架基团，骨架基团进一步包括反应性功能团，其中水不溶性水凝胶的特征在于，通过水解降解可将可降解键分解为可溶于水的降解产物，包括一个或多个骨架基团，完全降解水凝胶所需的时间与基于水凝胶中所有骨架基团数量的第一个10摩尔％可溶性降解产物的释放时间之比大于1且小于等于2。本发明还涉及这种水凝胶与配体或配位基团的共轭物、前药和制药组合物以及它们在药物中的使用。
• Protecting group comprising a purification tag
  申请人：Ascendis Pharma A/S

  公开号：US10040850B2

  公开（公告）日：2018-08-07

  The present invention relates to compounds comprising a protecting group moiety-tag moiety conjugate, a method of purification and monoconjugates obtained from such method of purification.

  本发明涉及包含保护基团-标记基团共轭物的化合物、纯化方法以及通过这种纯化方法获得的单体。
• BIODEGRADABLE POLYETHYLENE GLYCOL BASED WATER-INSOLUBLE HYDROGELS
  申请人：Ascendis Pharma A/S

  公开号：EP2459220B1

  公开（公告）日：2020-09-09