1H-苯并[d]咪唑-4-甲醛 | 144876-36-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1H-苯并[d]咪唑-4-甲醛
• 中文别名: 1H-苯并[D]咪唑-4-甲醛；咪唑并[1,2-a]吡啶-2-甲醛
• 英文名称: 1H-1,3-benzodiazole-4-carbaldehyde
• 英文别名: 1H-Benzo[d]imidazole-4-carbaldehyde；1H-benzimidazole-4-carbaldehyde
• CAS: 144876-36-8
• 化学式: C₈H₆N₂O
• mdl: MFCD10698555
• 分子量: 146.148
• InChiKey: UNGJRTXGRUDJGM-UHFFFAOYSA-N

物化性质

• 沸点：
  448.0±18.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1H-苯并[d]咪唑-4-甲醛 在 sodium tetrahydroborate 、 乙醇 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 N-((1H-benzo[d]imidazol-7-yl)methyl)-2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

  摘要：

  N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2' and 3'-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2'-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2'-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.011
• 作为产物：
  描述：

  苯并咪唑-7-羧酸甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1H-苯并[d]咪唑-4-甲醛
  参考文献：
  名称：

  一种亚胺类IDO抑制剂及其制备与用途

  摘要：

  本发明涉及一种亚胺类IDO抑制剂，它们的制备与治疗用途，所述亚胺类IDO抑制剂包括式I所示的亚胺类化合物或其药学上可接受的盐，其可以用作抗肿瘤免疫治疗药剂，式I所示取代基如说明书中描述，本发明的IDO抑制剂特点在于：作为IDO抑制剂，在细胞水平上的活性优异，其IC50小于1μM。

  公开号：

  CN114835621A

文献信息

• [EN] BICYCLIC HETEROARYL DERIVATIVES AS ECTONUCLEOTIDE PYROPHOSPHATASE PHOSPHODIESTERASE 1 INHIBITORS<br/>[FR] DÉRIVÉS HÉTÉROARYLE BICYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE L'ECTONUCLÉOTIDE PYROPHOSPHATASE/PHOSPHODIESTÉRASE 1
  申请人：RIBOSCIENCE LLC

  公开号：WO2020210649A1

  公开（公告）日：2020-10-15

  The present disclosure provides certain bicyclic heteroaryl compounds that inhibit ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) enzymatic activity and are therefore useful for the treatment of diseases and conditions modulated at least in part by ENPP1. In some embodiments, the bicyclic heteroaryl compounds includes those of Formula (I). Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本公开提供了一些抑制细胞外核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）酶活性的双环杂环芳基化合物，因此对于治疗至少部分受ENPP1调节的疾病和病况是有用的。在某些实施例中，双环杂环芳基化合物包括式（I）中的化合物。本文还提供了含有这类化合物的药物组合物以及制备这类化合物的方法。
• Rational Design of Novel Selective Dual-Target Inhibitors of Acetylcholinesterase and Monoamine Oxidase B as Potential Anti-Alzheimer’s Disease Agents
  作者：Yixiang Xu、Jian Zhang、Huan Wang、Fei Mao、Keting Bao、Wenwen Liu、Jin Zhu、Xiaokang Li、Haiyan Zhang、Jian Li

  DOI：10.1021/acschemneuro.8b00357

  日期：2019.1.16

  monoamine oxidases (MAOs) are promising therapy for Alzheimer's disease (AD). Herein, a series of novel propargylamine-modified pyrimidinylthiourea derivatives (1-4) were designed and synthesized as dual inhibitors of ChEs and MAOs with other functions against AD. Most of these derivatives inhibited ChEs and MAOs with IC50 values in the micro- or nanomolar ranges. Compound 1c displayed the dual functional profile

  针对胆碱酯酶（ChEs）和单胺氧化酶（MAOs）的多功能药物有望用于治疗阿尔茨海默氏病（AD）。在此，设计并合成了一系列新颖的炔丙基胺改性的嘧啶基硫脲衍生物（1-4），作为ChE和MAO的双重抑制剂，具有对AD的其他功能。这些衍生物大多数以微摩尔或纳摩尔范围的IC50值抑制Ch​​E和MAO。化合物1c显示了靶向AChE（IC50 = 0.032±0.007μM）和MAO-B（IC50 = 2.117±0.061μM）的双重功能谱，同时改善了血脑屏障（BBB）的通透性，抗氧化能力和良好的耐受性铜的体外螯合性能。动物研究表明，化合物1c·HCl可以抑制小鼠大脑AChE / MAO-B活性并减轻东amine碱引起的认知障碍。
• 一种预防和治疗冠心病的药物及其应用
  申请人：哈尔滨医科大学

  公开号：CN106916143B

  公开（公告）日：2019-09-27

  本发明涉及一种具有优良的卵磷脂‑胆固醇乙酰基转移酶(即LCAT)激活效应，优选可逆LCAT激活效应的吲哚啉酮衍生物或其药学上可接受的盐。这类化合物包括式I所示化合物或其药学上可接受的盐：本发明化合物对LCAT具有优异的激动效应，并且对于HDL水平有显著的增加作用，因此适合用于预防和治疗心脑血管疾病如冠心病、动脉硬化等。
• [EN] PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS<br/>[FR] PYRAZOLO[4,3-D]PYRIMIDINES UTILES EN TANT QU'INHIBITEURS DE KINASES
  申请人：ORIGENIS GMBH

  公开号：WO2014060112A1

  公开（公告）日：2014-04-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及具有式（I）的新化合物，其能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物可用于治疗多种疾病。这些疾病包括自身免疫疾病、炎症性疾病、骨疾病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和激素相关疾病。
• [EN] COMPOSITIONS AND METHODS FOR TREATING DISORDERS OF CIRCADIAN AND DIURNAL RHYTHMS USING PROKINETICIN 2 AGONISTS AND ANTAGONISTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE TRAITEMENT DES TROUBLES DES RYTHMES CIRCADIEN ET DIURNE AU MOYEN D'AGONISTES ET D'ANTAGONISTES DE PROKINÉTICINE 2
  申请人：UNIV CALIFORNIA

  公开号：WO2017177026A1

  公开（公告）日：2017-10-12

  In alternative embodiments, provided are methods for: modifying circadian rhythmicity or timing in a mammal, treating psychiatric conditions or symptoms due to alterations in a human circadian regulatory system, treating sleep problems in a mammal, or inducing sleep or activity suppression, or causing an arousal or wakening reaction, comprising administration to a mammal or human a compound or composition capable of modifying a prokineticin 2 (PK2) expression or activity, and/or a PKR2 (PK2 receptor), a vasopressin receptor (VR), and/or a melatonin receptor (MR) expression or activity.

  在另一种实施方式中，提供了以下方法：修改哺乳动物的昼夜节律或时机，治疗由于人类昼夜节律调节系统变化引起的精神疾病或症状，治疗哺乳动物的睡眠问题，或诱导睡眠或活动抑制，或引起唤醒反应，包括向哺乳动物或人类给予能够修改促动素2（PK2）表达或活性，和/或PKR2（PK2受体），血管加压素受体（VR）和/或褪黑素受体（MR）表达或活性的化合物或组合物。