1-[2-(adamantan-1-yl)-2-hydroxyethyl]imidazole | 64310-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[2-(adamantan-1-yl)-2-hydroxyethyl]imidazole
• 英文别名: 2-(1H-imidazol-1-yl)-1-tricyclo[3.3.1.13,7]dec-1-yl-ethanol；1-[2-(1-adamantyl)-2-hydroxyethyl]imidazole；1-adamantan-1-yl-2-imidazol-1-yl-ethanol；1-(1-Adamantyl)-2-imidazol-1-yl-ethanol；1-(1-adamantyl)-2-imidazol-1-ylethanol
• CAS: 64310-42-5
• 化学式: C₁₅H₂₂N₂O
• mdl: MFCD16235897
• 分子量: 246.352
• InChiKey: CPYRWQXGEGGVIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二氯氯苄 、 1-[2-(adamantan-1-yl)-2-hydroxyethyl]imidazole 以 六甲基磷酰三胺 、 二氯甲烷 、 mineral oil 为溶剂， 生成 1-[2-(1-adamantyl)-2-(2,4-dichlorobenzyloxy)ethyl]imidazole
  参考文献：
  名称：

  1-[2-(1-Adamantyl)-2-(R-thio)ethyl]imidazoles and

  摘要：

  式为##STR1##的化合物，其中R是烷基、环烷基、环烷基烷基、苯基或苯基烷基，所述苯基和苯基烷基在苯环上可选择地被一个或多个取代基取代，所述取代基独立地选自卤素、烷基和三氟甲基; X为氧或硫，但当R为苯基或取代苯基时，X不是氧; 以及其抗菌酸盐酸盐在抗真菌、抗菌和抗原虫药物中有用。

  公开号：

  US04036975A1
• 作为产物：
  描述：

  1-金刚烷基溴甲酮 以 N-甲基乙酰胺 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 1-[2-(adamantan-1-yl)-2-hydroxyethyl]imidazole
  参考文献：
  名称：

  1-[2-(1-Adamantyl)-2-(R-thio)ethyl]imidazoles and

  摘要：

  式为##STR1##的化合物，其中R是烷基、环烷基、环烷基烷基、苯基或苯基烷基，所述苯基和苯基烷基在苯环上可选择地被一个或多个取代基取代，所述取代基独立地选自卤素、烷基和三氟甲基; X为氧或硫，但当R为苯基或取代苯基时，X不是氧; 以及其抗菌酸盐酸盐在抗真菌、抗菌和抗原虫药物中有用。

  公开号：

  US04036975A1

文献信息

• Novel Structural Insight into Inhibitors of Heme Oxygenase-1 (HO-1) by New Imidazole-Based Compounds: Biochemical and In Vitro Anticancer Activity Evaluation
  作者：Khaled Greish、Loredana Salerno、Reem Al Zahrani、Emanuele Amata、Maria Modica、Giuseppe Romeo、Agostino Marrazzo、Orazio Prezzavento、Valeria Sorrenti、Antonio Rescifina、Giuseppe Floresta、Sebastiano Intagliata、Valeria Pittalà

  DOI：10.3390/molecules23051209

  日期：——

  In this paper, the design, synthesis, and molecular modeling of a new azole-based HO-1 inhibitors was reported, using compound 1 as a lead compound, in which an imidazole moiety is linked to a hydrophobic group by means of an ethanolic spacer. The tested compounds showed a good inhibitor activity and possessed IC50 values in the micromolar range. These results were obtained by targeting the hydrophobic

  在本文中，报道了一种新型唑类 HO-1 抑制剂的设计、合成和分子建模，使用化合物 1 作为先导化合物，其中咪唑部分通过乙醇间隔键连接到疏水基团. 受试化合物显示出良好的抑制剂活性，并具有微摩尔范围内的 IC50 值。这些结果是通过靶向疏水性西部区域获得的。分子建模研究证实了一种巩固的结合模式，其中咪唑基部分的氮与血红素亚铁相配位，同时疏水基团位于 HO-1 结合口袋的西部区域。此外，对新化合物进行了计算机模拟 ADME-Tox 特性的筛选，以预测具有令人信服的结果的类药物行为。最后，在不同的癌细胞系中研究了化合物 1 的体外抗肿瘤活性特征，并合成了纳米胶束制剂，目的是提高化合物 1 的水溶性。最后，化合物 1 与多柔比星联合在黑色素瘤细胞中进行了测试，显示出有趣的协同活性。
• Imidazole derivatives and salts thereof and pharmaceutical formulations
  申请人：Burroughs Wellcome Co.

  公开号：US04328234A1

  公开（公告）日：1982-05-04

  Imidazoles of formula (I) ##STR1## wherein A is a chemical bond or a straight or branched, saturated or unsaturated, aliphatic residue having from 1 to 6 carbon atoms wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatoms or heteroatoms R is a fused, saturated or unsaturated, non-aromatic carbocyclic, polycyclic ring system; a saturated or unsaturated, carbocyclic spirocyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen; or a saturated or unsaturated, carbocyclic bridged-polycyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen and having one or more bridges; or AR together represent a straight or branched, saturated or unsaturated, aliphatic residue having 3 to 6 carbon atoms, wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatom or heteroatoms; which aliphatic residue is substituted by at least two groups, which may be the same or different, selected from the groups specified for R above. and acid addition salts and pharmaceutically acceptable bioprecursors thereof. Methods of preparing the imidazoles are disclosed. The imidazoles and their acid addition salts and bioprecursors are useful in the treatment or prophylaxis of thrombo-embolic conditions.

  Imidazoles的化学式（I）##STR1##其中A是化学键或直链或支链、饱和或不饱和的、具有1至6个碳原子的脂肪残基，其中这些碳原子中的1、2或3个可以被氧、硫和氮等异原子取代，提供（在2或3个异原子的情况下）任何这样的异原子不位于另一个这样的异原子或异原子旁边R是融合的、饱和的或不饱和的、非芳香性碳环多环环系统；一个饱和或不饱和的、碳环螺环系统，可选地含有一个或多个氧、硫和氮等环异原子；或者是一个饱和或不饱和的、碳环桥联多环环系统，可选地含有一个或多个氧、硫和氮等环异原子并具有一个或多个桥梁；或者AR一起表示一个直链或支链、饱和或不饱和、具有3至6个碳原子的脂肪残基，其中这些碳原子中的1、2或3个可以被氧、硫和氮等异原子取代，提供（在2或3个异原子的情况下）任何这样的异原子不位于另一个这样的异原子或异原子旁边；这种脂肪残基被至少两个可能相同或不同的从上述R中指定的基团取代。其酸盐和药学上可接受的生物前体。揭示了制备咪唑的方法。咪唑及其酸盐和生物前体在治疗或预防血栓栓塞症方面是有用的。
• 1-substituted imidazoles, and salts thereof, a method for their preparation and pharmaceutical formulations thereof
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0015002A1

  公开（公告）日：1980-09-03

  Imidazoles of formula (I) wherein A is a chemical bond or a straight or branched, saturated or unsaturated, aliphatic residue having from 1 to 6 carbon atoms, optionally substituted and/or optionally including 1, 2 or3 heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatom or heteroatoms, the total number of said carbon atoms and heteroatoms not exceeding 6. R is a fused, saturated or unsaturated, non-aromatic carbocyclic, bi- or tri-cyclic ring system providing that when R is a 9- decahydronaphthyl group, A does not represent a carbonyl group, a saturated or unsaturated, carbocyclic spirocyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen; or a saturated or unsaturated. carbocyclic bridged-polycyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen and having one or more bridges providing that when R is an adamantanyl group, A does not represent an ethylene radical (-(CH2)2-) substituted at the carbon atom a to the adamantanyl group by a hydroxy, oxo, ether or thioether grouping; or AR together represent a straight or branched, saturated or unsaturated, aliphatic residue having 3 to 6 carbon atoms, optionally substituted and/or optionally including 1, 2 or 3 heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatom or heteroatoms, the total number of said carbon and heteroatoms not exceeding 6; which aliphatic residue is substituted by at least two groups, which may be the same or different, selected from the groups specified for R above and acid addition salts and pharmaceutically acceptable bioprecursors thereof. Methods of preparing the imidazoles are disclosed The imidazoles and their acid addition salts an bioprecur. sors are useful in the treatment of prophylaxis of thrombo- embolic conditions.

  式(I)的咪唑 其中 A 是化学键或直链或支链、饱和或不饱和、脂肪族残基，具有 1 至 6 个碳原子，任选被取代和/或任选包括 1、2 或 3 个选自氧、硫和氮的杂原子，条件是（在 2 或 3 个杂原子的情况下）任何此类杂原子不与另一个或多个此类杂原子相邻，所述碳原子和杂原子的总数不超过 6。 R 是融合的、饱和或不饱和的、非芳香族碳环、双环或三环的环系统，但当 R 是 9-十氢萘基时，A 不代表羰基、饱和或不饱和的碳环螺环系统，可选地含有一个或多个选自氧、硫和氮的环杂原子；或饱和或不饱和的碳环桥聚环系统。(b) 碳环桥式多环环系统，可选择含有一个或多个选自氧、硫和氮的环杂原子，并 具有一个或多个桥，条件是当 R 为金刚烷基时，A 不代表在金刚烷基的碳原子 a 处被羟基、氧代、醚或硫醚基团取代的乙烯基 (-(CH2)2-)；或 AR 共同代表直链或支链、饱和或不饱和、具有 3 至 6 个碳原子的脂族残基，可选被取代和/或可选包括 1、2 或 3 个选自氧、硫和氮的杂原子，前提是（在 2 或 3 个杂原子的情况下）任何此类杂原子不与另一个或多个此类杂原子相邻，所述碳原子和杂原子的总数不超过 6；该脂肪族残基被至少两个基团取代，这两个基团可以相同或不同，选自上述 R 所指的基团及其酸加成盐和药学上可接受的生物前体。 已公开咪唑的制备方法 咪唑类及其酸加成盐和生物前体可用于血栓栓塞的预防治疗。
• US4036975A
  申请人：——

  公开号：US4036975A

  公开（公告）日：1977-07-19
• US4328234A
  申请人：——

  公开号：US4328234A

  公开（公告）日：1982-05-04