N-methyl-4-benzofuranmethanamine | 121212-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-methyl-4-benzofuranmethanamine
• 英文别名: 1-(benzofuran-4-yl)-N-methylmethanamine；1-(Benzofuran-4-yl)-N-methylmethanamine；1-(1-benzofuran-4-yl)-N-methylmethanamine
• CAS: 121212-17-7
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: BFJWVISBCJLQFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-4-benzofuranmethanamine 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以94%的产率得到N-methyl-4-(2,3-dihydrobenzofuranyl)amine
  参考文献：
  名称：

  Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof

  摘要：

  本发明涉及一种治疗包括认知障碍、广泛性焦虑障碍、急性应激障碍、社交恐惧症、简单恐惧症、经前期情绪性失调障碍、社交焦虑障碍、重度抑郁障碍、进食障碍、肥胖症、厌食症、暴食症、物质滥用障碍、化学依赖、尼古丁成瘾、可卡因成瘾、酒精成瘾、安非他命成瘾、莱什-尼汉综合征、神经退行性疾病、月经后期综合征、嗜睡症、精神症状愤怒、拒绝敏感性、运动障碍、锥体外症候群、抽动障碍、不安腿综合征、迟发性运动障碍、与睡眠相关的进食障碍、夜间进食综合征、压力性尿失禁、偏头痛、神经痛、糖尿病性神经病变、纤维肌痛综合征、慢性疲劳综合征、性功能障碍、早泄和男性阳痿等多种疾病的方法。该方法涉及向需要此类治疗的患者施用所述化合物的治疗有效量。这些化合物是具有以下IA、IB、IIA、IIB、IIIA或IIIC式的4-苯基取代四氢异喹啉。

  公开号：

  US20060111385A1
• 作为产物：
  描述：

  苯并呋喃-4-甲腈 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-methyl-4-benzofuranmethanamine
  参考文献：
  名称：

  Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections

  摘要：

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.

  DOI：

  10.1021/acs.jmedchem.5b01984

文献信息

• Highly selective .kappa.-opioid analgesics. 2. Synthesis and structure activity relationships of novel N-(2-aminocyclohexyl)arylacetamide derivatives
  作者：Paul R. Halfpenny、Raymond G. Hill、David C. Horwell、John Hughes、John C. Hunter、Stephen Johnson、David C. Rees

  DOI：10.1021/jm00127a036

  日期：1989.7

  chemical synthesis and the development of structure-activity relationships (SAR) for the kappa opioid receptor affinity and mu/kappa opioid receptor selectivity of novel N-[(2-aminocyclohexyl)aryl]acetamide derivatives. The SAR of this series are investigated by consideration of structural modifications made to the aromatic moiety, the amide linkage, and cyclohexane and the pyrrolidine ring substituents

  本文描述了新型N-[（2-氨基环己基）芳基]乙酰胺衍生物的κ阿片受体亲和力和mu / k阿片受体选择性的化学合成和结构-活性关系（SAR）的发展。通过考虑对原型kappa选择性激动剂PD117302（反式-N-甲基-N- [2-（ 1-吡咯烷基）环己基]苯并[b]噻吩-4-乙酰胺）（1）。报道了23种新化合物的Kappa和mu阿片受体结合亲和力。观察到，通过C-4位连接的苯并[b]噻吩芳族系统获得了最佳的mu / kappa受体选择性，根据空间和电子参数进行讨论。酰胺键已被反向酰胺，酯，氨基亚甲基，硫代酰胺和仲酰胺取代。这些等排物中最好的是N-甲基酰胺。与未取代的化合物，例如化合物14，反式-（+/-）-N-甲基-N- [2- []相比，PD117302的吡咯烷环在3-位被羟基亚甲基取代提高了mu /κ选择性。 3-（羟甲基）-1-吡咯烷基]环己基] -4-苯并[b]呋喃乙酰胺单盐酸盐，mu
• Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof
  申请人：Molino F. Bruce

  公开号：US20060111385A1

  公开（公告）日：2006-05-25

  The present invention relates to a method of treating disorders including cognition impairment, generalized anxiety disorder, acute stress disorder, social phobia, simple phobias, pre-menstrual dysphoric disorder, social anxiety disorder, major depressive disorder, eating disorders, obesity, anorexia nervosa, bulimia nervosa, binge eating disorder, substance abuse disorders, chemical dependencies, nicotine addiction, cocaine addiction, alcohol addiction, amphetamine addiction, Lesch-Nyhan syndrome, neurodegenerative diseases, late luteal phase syndrome, narcolepsy, psychiatric symptoms anger, rejection sensitivity, movement disorders, extrapyramidal syndrome, Tic disorder, restless leg syndrome, tardive dyskinesia, sleep related eating disorder, night eating syndrome, stress urinary incontinence, migraine, neuropathic pain, diabetic neuropathy, fibromyalgia syndrome, chronic fatigue syndrome, sexual dysfunction, premature ejaculation, and male impotence. This method involves administering to a patient in need of such treatment a therapeutically effective amount of a disclosed compound. Such compounds are 4-phenyl substituted tetrahydroisoquinolines having the Formula IA, IB, IIA, IIB, IIIA or IIIC as set forth herein.

  本发明涉及一种治疗包括认知障碍、广泛性焦虑障碍、急性应激障碍、社交恐惧症、简单恐惧症、经前期情绪性失调障碍、社交焦虑障碍、重度抑郁障碍、进食障碍、肥胖症、厌食症、暴食症、物质滥用障碍、化学依赖、尼古丁成瘾、可卡因成瘾、酒精成瘾、安非他命成瘾、莱什-尼汉综合征、神经退行性疾病、月经后期综合征、嗜睡症、精神症状愤怒、拒绝敏感性、运动障碍、锥体外症候群、抽动障碍、不安腿综合征、迟发性运动障碍、与睡眠相关的进食障碍、夜间进食综合征、压力性尿失禁、偏头痛、神经痛、糖尿病性神经病变、纤维肌痛综合征、慢性疲劳综合征、性功能障碍、早泄和男性阳痿等多种疾病的方法。该方法涉及向需要此类治疗的患者施用所述化合物的治疗有效量。这些化合物是具有以下IA、IB、IIA、IIB、IIIA或IIIC式的4-苯基取代四氢异喹啉。
• Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant <i>Staphylococcus aureus</i> (MRSA) Infections
  作者：Youxin Wang、Feifei Chen、Hongxia Di、Yong Xu、Qiang Xiao、Xuehai Wang、Hanwen Wei、Yanli Lu、Lingling Zhang、Jin Zhu、Chunquan Sheng、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.5b01984

  日期：2016.4.14

  Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 mu M). Notably, compound 5m (1 mu M) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 mu g/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.