N-(3-hydroxybenzyl)isopropylamine | 213891-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-hydroxybenzyl)isopropylamine
• 英文别名: 3-{[(Propan-2-yl)amino]methyl}phenol；3-[(propan-2-ylamino)methyl]phenol
• CAS: 213891-23-7
• 化学式: C₁₀H₁₅NO
• mdl: MFCD11139278
• 分子量: 165.235
• InChiKey: LMRDSYOGDQTGMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxybenzyl)isopropylamine 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 39.0h， 生成 3-[({3-[(9-oxo-9H-xanthen-3-yl)oxy]propyl}(propan-2-yl)amino)methyl]phenyl N-butylcarbamate
  参考文献：
  名称：

  Acetylcholinesterase Inhibitors:  Synthesis and Structure−Activity Relationships of ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl Derivatives

  摘要：

  Acetylcholinesterase (AChE) inhibitors are one of the most actively investigated classes of compounds in the search for an effective treatment of Alzheimer's disease. This work describes the synthesis, AChE inhibitory activity, and structure-activity relationships of some compounds related to a recently discovered series of AChE inhibitors: the omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyxanthen-9-ones. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different parts of the parent molecule, and a theoretical model of the binding of one representative compound to the enzyme was developed. The biological properties of the series were investigated in some detail by considering not only the activity on isolated enzyme but the selectivity with respect to butyrylcholinesterase (BuChE) and the in vitro inhibitory activity on rat cerebral cortex as well. Some of the newly synthesized derivatives, when tested on isolated and/or AChE-enriched rat brain cortex fraction, displayed a selective inhibitory activity and were more active than physostigmine. In particular, compound 13, an azaxanthone derivative, displayed the best rat cortex AChE inhibition (190-fold higher than physostigmine), as well as a high degree of enzyme selectivity (over 60-fold more selective for AChE than for BuChE). When tested in the isolated enzyme, compound 13 was less active, suggesting some differences either in drug availability/biotransformation or in the inhibitor-sensitive residues of the enzyme when biologically positioned in rat brain membranes.

  DOI：

  10.1021/jm9810046
• 作为产物：
  描述：

  间羟基苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 N-(3-hydroxybenzyl)isopropylamine
  参考文献：
  名称：

  Acetylcholinesterase Inhibitors:  Synthesis and Structure−Activity Relationships of ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl Derivatives

  摘要：

  Acetylcholinesterase (AChE) inhibitors are one of the most actively investigated classes of compounds in the search for an effective treatment of Alzheimer's disease. This work describes the synthesis, AChE inhibitory activity, and structure-activity relationships of some compounds related to a recently discovered series of AChE inhibitors: the omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyxanthen-9-ones. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different parts of the parent molecule, and a theoretical model of the binding of one representative compound to the enzyme was developed. The biological properties of the series were investigated in some detail by considering not only the activity on isolated enzyme but the selectivity with respect to butyrylcholinesterase (BuChE) and the in vitro inhibitory activity on rat cerebral cortex as well. Some of the newly synthesized derivatives, when tested on isolated and/or AChE-enriched rat brain cortex fraction, displayed a selective inhibitory activity and were more active than physostigmine. In particular, compound 13, an azaxanthone derivative, displayed the best rat cortex AChE inhibition (190-fold higher than physostigmine), as well as a high degree of enzyme selectivity (over 60-fold more selective for AChE than for BuChE). When tested in the isolated enzyme, compound 13 was less active, suggesting some differences either in drug availability/biotransformation or in the inhibitor-sensitive residues of the enzyme when biologically positioned in rat brain membranes.

  DOI：

  10.1021/jm9810046

文献信息

• Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate
  作者：Hiroki Nakayama、Shingo Harada、Masato Kono、Tetsuhiro Nemoto

  DOI：10.1021/jacs.7b04813

  日期：2017.8.2

  dearomatization of phenols using Ag carbenoids from α-diazoacetamides. The Ag catalyst promoted intramolecular dearomatization of phenols, whereas a Rh or Cu catalyst caused C-H insertion and a Büchner reaction. Studies indicated Ag carbenoids have a carbocation-like character, making their behavior and properties unique. Highly enantioselective transformations using Ag carbenoids have not been reported. We achieved

  我们报告了使用来自 α-重氮乙酰胺的 Ag 卡宾对苯酚进行不对称脱芳构化。Ag 催化剂促进酚类的分子内脱芳构化，而 Rh 或 Cu 催化剂引起 CH 插入和 Büchner 反应。研究表明，银类卡宾具有类似碳正离子的特性，使其行为和特性独一无二。尚未报道使用 Ag 卡宾的高度对映选择性转化。我们首次实现了具有底物通用性的 Ag 卡宾介导的化学和高度对映选择性苯酚脱芳构化。
• PHENYLPYRAZOLE DERIVATIVES AS POTENT ROCK1 AND ROCK2 INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：US20140243338A1

  公开（公告）日：2014-08-28

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式(I)的化合物：或其立体异构体、互变异构体或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用这些药物组合物治疗心血管、平滑肌、肿瘤学、神经病理学、自身免疫、纤维化和/或炎症性疾病的方法。
• NOVEL BICYCLIC NITROGEN CONTAINING HETEROARYL TGR5 RECEPTOR MODULATORS
  申请人：Robl Jeffrey A.

  公开号：US20140080788A1

  公开（公告）日：2014-03-20

  Novel compounds of Formula I:or an enantiomer, diastereomer, tautomer, prodrug or salt thereof, wherein m, Q, T, U, V, ring A, X, Y, R 3 , R 4 , R 4a , R 5a , R 5b , R 5c , R 5d , R 5e , R 6a , R 6b , and R 6c are defined herein, are provided which are TGR5 G protein-coupled receptor modulators. TGR5 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring TGR5 G protein-coupled receptor modulator therapy. Thus, the disclosure also concerns compositions comprising these novel compounds and methods of treating diseases or conditions related to the activity of the TGR5 G protein-coupled receptor by using any of these novel compounds or a composition comprising any of such novel compounds.

  本发明提供了一种公式I的新化合物：或其对映异构体、顺反异构体、互变异构体、前药或其盐，其中m、Q、T、U、V、环A、X、Y、R3、R4、R4a、R5a、R5b、R5c、R5d、R5e、R6a、R6b和R6c的定义如本文所述，这些化合物是TGR5 G蛋白偶联受体调节剂。 TGR5 G蛋白偶联受体调节剂在治疗、预防或减缓需要TGR5 G蛋白偶联受体调节剂治疗的疾病方面具有用途。因此，本公开还涉及包含这些新化合物的组合物以及使用任何这些新化合物或包含任何这些新化合物的组合物来治疗与TGR5 G蛋白偶联受体活性相关的疾病或病症的方法。
• PURINE DERIVATIVE COMPOUNDS FOR MEDICAL USE
  申请人：MANROS THERAPEUTICS

  公开号：US20150320753A1

  公开（公告）日：2015-11-12

  A method for treatment of disease by reduction in macrophages-mediated bacterial killing, including administration to patients in need a compound of formula (I): wherein A is N or CH; B is NO, or S; R 1 is H, (C 1 -C 4 )alkyl group, methyl(C 1 -C 6 )cycloalkyl group or (C 1 -C 6 )cycloalkyl group; R 2 is an aryl, arylmethyl group or methylheteroaryl group as methylpyridine and methylthiophene; R 3 is absent when B is O or S, or is H or (C 1 -C 4 )alkyl group when B is N; R 4 is (C 1 -C 5 )alkyl group or (C 1 -C 4 )cycloalkyl group, groups bearing a carboxylic acid group, and (C 1 -C 5 )alkyl group or (C 1 -C 4 )cycloalkyl substituted by hydroxyl group, halogen group or methoxy group, when B is N, R 3 and R 4 can together form a 5- or 6-membered heterocycle substituted by carboxylic acid group, substituted by a halogen atom, hydroxyl group, methoxy group or hydroxymethyl group, or pharmaceutically acceptable salt. Also provided are new compounds relating to this use.

  一种通过减少巨噬细胞介导的细菌杀伤治疗疾病的方法，包括向需要治疗的患者给予式(I)的化合物：其中A是N或CH；B是NO或S；R1是H，(C1-C4)烷基，甲基(C1-C6)环烷基或(C1-C6)环烷基；R2是芳基，芳基甲基基或甲基杂环芳基，如甲基吡啶和甲基噻吩；当B为O或S时，R3不存在，或者当B为N时，R3是H或(C1-C4)烷基；R4是(C1-C5)烷基或(C1-C4)环烷基，带有羧酸基团，以及(C1-C5)烷基或(C1-C4)环烷基被羟基基团，卤素基团或甲氧基团取代，当B为N时，R3和R4可以共同形成一个被羧酸基团取代的5-或6-成员杂环，在卤素原子，羟基基团，甲氧基团或羟甲基基团取代。还提供了与此用途相关的新化合物。
• Purine derivative compounds for medical use
  申请人：Manros Therapeutics

  公开号：EP2907514B1

  公开（公告）日：2019-10-23