1-isopropyl-6-(1-methoxybutan-2-yloxy)-1H-benzo[d]-imidazol-4-amine | 1262957-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-isopropyl-6-(1-methoxybutan-2-yloxy)-1H-benzo[d]-imidazol-4-amine
• 英文别名: 6-(1-Methoxybutan-2-yloxy)-1-propan-2-ylbenzimidazol-4-amine
• CAS: 1262957-45-8
• 化学式: C₁₅H₂₃N₃O₂
• 分子量: 277.367
• InChiKey: DLEVKZBCCQLVGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-isopropyl-6-(1-methoxybutan-2-yloxy)-1H-benzo[d]-imidazol-4-amine 、 苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 26.0h， 以76%的产率得到N-benzyl-1-isopropyl-6-(1-methoxybutan-2-yloxy)-1H-benzo[d]imidazol-4-amine
  参考文献：
  名称：

  Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25

  摘要：

  Alzheimer's disease (AD) is a progressive neurodegenerative disease resulting in cognitive and behavioral impairment. The two classic pathological hallmarks of AD include extraneuronal deposition of amyloid beta (A beta) and intraneuronal formation of neurofibrillary tangles (NFTs). NFTs contain hyperphosphorylated tau. Tau is the major microtubule-associated protein in neurons and stabilizes microtubules (MTs). Cyclin dependent kinase 5 (CDK5), when activated by the regulatory binding protein p25, phosphorylates tau at a number of proline-directed serine/threonine residues, resulting in formation of phosphorylated tau as paired helical filaments (PHFs) then in subsequent deposition of PHFs as NFTs. Beginning with the structure of Roscovitine, a moderately selective CDK5 inhibitor, we sought to conduct structural modifications to increase inhibitory potency of CDK5 and increase selectivity over a similar enzyme, cyclin dependent kinase 2 (CDK2). The design, synthesis, and testing of a series of 1-isopropyl-4-aminobenzyl-6-ether-linked benzimidazoles is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.022
• 作为产物：
  描述：

  1-isopropyl-6-(1-methoxybutan-2-yloxy)-4-nitro-1H-benzo-[d]imidazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 23.0 ℃ 、344.75 kPa 条件下， 反应 12.0h， 生成 1-isopropyl-6-(1-methoxybutan-2-yloxy)-1H-benzo[d]-imidazol-4-amine
  参考文献：
  名称：

  Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25

  摘要：

  Alzheimer's disease (AD) is a progressive neurodegenerative disease resulting in cognitive and behavioral impairment. The two classic pathological hallmarks of AD include extraneuronal deposition of amyloid beta (A beta) and intraneuronal formation of neurofibrillary tangles (NFTs). NFTs contain hyperphosphorylated tau. Tau is the major microtubule-associated protein in neurons and stabilizes microtubules (MTs). Cyclin dependent kinase 5 (CDK5), when activated by the regulatory binding protein p25, phosphorylates tau at a number of proline-directed serine/threonine residues, resulting in formation of phosphorylated tau as paired helical filaments (PHFs) then in subsequent deposition of PHFs as NFTs. Beginning with the structure of Roscovitine, a moderately selective CDK5 inhibitor, we sought to conduct structural modifications to increase inhibitory potency of CDK5 and increase selectivity over a similar enzyme, cyclin dependent kinase 2 (CDK2). The design, synthesis, and testing of a series of 1-isopropyl-4-aminobenzyl-6-ether-linked benzimidazoles is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.022

文献信息

• HETEROCYCLIC COMPOUND AND AGRICULTURAL OR HORTICULTURAL FUNGICIDE
  申请人：Nippon Soda Co., Ltd.

  公开号：US20220142165A1

  公开（公告）日：2022-05-12

  A compound of formula (I) (in the formula (I), R 1 represents a substituted or unsubstituted C1-6 alkyl group or the like, R 2 represents a substituted or unsubstituted 5- or 6-membered heteroaryl group, R 3 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group or the like, Y represents an oxygen atom or NH, A 1 represents a sulfur atom, an oxygen atom, or NR 4 , R 4 represents a C1-6 alkyl group, A 2 is a carbon atom or a nitrogen atom, X represents a substituent, n represents the chemically acceptable number of X, and is an integer of 0 to 3, and, when n is 2 or more, X may be identical to or different from each other), or a salt thereof is provided.

  提供式(I)的化合物（在式(I)中，R1代表取代或未取代的C1-6烷基或类似物，R2代表取代或未取代的5-或6-成员杂芳基团，R3代表取代或未取代的C1-6烷基，取代或未取代的C1-6烷氧羰基团或类似物，Y代表氧原子或NH，A1代表硫原子，氧原子或NR4，R4代表C1-6烷基，A2是碳原子或氮原子，X代表取代基，n代表X的化学上可接受的数量，且为0到3的整数，当n为2或更多时，X可以相同或不同），或其盐。
• HETEROCYCLIC COMPOUND AND AGRICULTURAL OR HORTICULTURAL BACTERICIDE
  申请人：Nippon Soda Co., Ltd.

  公开号：EP3939975A1

  公开（公告）日：2022-01-19

  A compound of formula (I) (in the formula (I), R1 represents a substituted or unsubstituted C1-6 alkyl group or the like, R2 represents a substituted or unsubstituted 5- or 6-membered heteroaryl group, R3 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group or the like, Y represents an oxygen atom or NH, A1 represents a sulfur atom, an oxygen atom, or NR4, R4 represents a C1-6 alkyl group, A2 is a carbon atom or a nitrogen atom, X represents a substituent, n represents the chemically acceptable number of X, and is an integer of 0 to 3, and, when n is 2 or more, X may be identical to or different from each other), or a salt thereof is provided.

  式（I）化合物（式（I）中，R1 代表取代或未取代的 C1-6 烷基或类似基团，R2 代表取代或未取代的 5 或 6 元杂芳基，R3 代表取代或未取代的 C1-6 烷基、取代或未取代的 C1-6 烷氧羰基或类似基团，Y 代表氧原子或 NH、A1代表硫原子、氧原子或NR4，R4代表C1-6烷基，A2是碳原子或氮原子，X代表取代基，n代表X的化学上可接受的数目，并且是0至3的整数，当n为2或更多时，X可以彼此相同或不同），或提供其盐。
• [EN] HETEROCYCLIC COMPOUND AND AGRICULTURAL OR HORTICULTURAL BACTERICIDE<br/>[FR] COMPOSÉ HÉTÉROCYCLIQUE ET BACTÉRICIDE AGRICOLE OU HORTICOLE<br/>[JA] 複素環化合物および農園芸用殺菌剤
  申请人：NIPPON SODA CO

  公开号：WO2020189525A1

  公开（公告）日：2020-09-24

  式（I）（式（I）中、Ｒ1は置換若しくは無置換のＣ１～６アルキル基などであり、Ｒ2は置換若しくは無置換の５～６員ヘテロアリール基であり、Ｒ3は置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシカルボニル基などであり、Ｙは酸素原子またはＮＨであり、Ａ1は硫黄原子、酸素原子またはＮＲ4であり、Ｒ4はＣ１～６アルキル基であり、Ａ2は炭素原子または窒素原子であり、Ｘは置換基であり、ｎは化学的に許容されるＸの個数を示しかつ０～３のいずれかの整数であり、且つｎが２以上のときＸは互いに同じでも異なってもよい。）で表される化合物、またはその塩が提供される。