2-甲氧基-4-硝苄基乙醇 | 136507-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-4-硝苄基乙醇
• 英文名称: 2-methoxy-4-nitrobenzyl alcohol
• 英文别名: (2-methoxy-4-nitrophenyl)methanol
• CAS: 136507-14-7
• 化学式: C₈H₉NO₄
• mdl: MFCD08277262
• 分子量: 183.164
• InChiKey: IWXYLEKOKGKRTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-甲氧基-4-硝苄基乙醇 在 氢溴酸 、 溶剂黄146 作用下， 生成 1-(溴甲基)-2-甲氧基-4-硝基苯
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  (2-Methoxy-4-nitrophenyl)methyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-甲氧基-4-硝苄基乙醇
  参考文献：
  名称：

  口服活性CCR5拮抗剂，作为抗HIV-1药物2：含有吡啶N-氧化物部分的苯胺衍生物的合成和生物活性。

  摘要：

  为了开发口服活性CCR5拮抗剂，我们研究了含有新的极性取代基（例如膦酸酯，氧化膦或吡啶N-氧化物部分）的1-苯并benzo庚因衍生物，以取代先前报道的季铵部分。在这些化合物中，2-（α-羟基苄基）吡啶N-氧化物5e在大鼠中表现出中等的CCR5拮抗活性并具有可接受的药代动力学特征。随后进行了化学修饰，发现具有（S）-构型羟基的化合物（S）-5f比（R）-异构体更具活性。用具有4- [2-（丁氧基）乙氧基]苯基的1-苯并ze庚因环替换具有4-甲基苯基的1-苯并x庚因环增强了结合测定中的活性。此外，在苯胺部分的苯基上引入3-三氟甲基导致HIV-1包膜介导的膜融合测定的活性大大提高。特别是，化合物（S）-5s在融合试验中显示出最强的CCR5拮抗活性（IC（50）= 7.2 nM）和抑制作用（IC（50）= 5.4 nM），并且在大鼠中具有良好的药代动力学特性。

  DOI：

  10.1248/cpb.52.818

文献信息

• PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS
  申请人：Arora Nidhi

  公开号：US20120015962A1

  公开（公告）日：2012-01-19

  Compounds of the formula I or II: wherein X, m, Ar, R 1 and R 2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

  式I或II的化合物： 其中X，m，Ar，R1和R2如本文所定义。所述化合物对于治疗IRAK介导的疾病是有用的。
• [EN] QUINAZOLINE DERIVATIVES FOR USE AGAINST CANCER<br/>[FR] DERIVES DE QUINAZOLINE A UTILISER CONTRE LE CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2006040526A1

  公开（公告）日：2006-04-20

  The invention concerns quinazoline derivatives of Formula (I) or a pharmaceutically-acceptable salt, solvate or pro-drug thereof, wherein each of p, R1, q, R2, R3, R4, R5, Ring A, X1, R6, r and R7 has any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders or in the treatment of disease states associated with angiogenesis and/or vascular permeability.

  本发明涉及式(I)喹唑啉衍生物或其药物可接受的盐、溶剂化物或前药，其中p、R1、q、R2、R3、R4、R5、环A、X1、R6、r和R7各自具有说明书中定义的任何含义；其制备方法、含有它们的药物组合物以及它们在制造用于治疗细胞增殖障碍或治疗与血管生成和/或血管通透性相关的疾病状态的药物中的应用。
• Vanilloid receptor ligands and their use in treatments
  申请人：——

  公开号：US20030195201A1

  公开（公告）日：2003-10-16

  Compounds having the general structure 1 and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有一般结构1的化合物以及含有它们的组合物，用于治疗急性疼痛、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、丛集性头痛、混合性血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定的膀胱病、银屑病、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛及其相关的过度疼痛和异常疼痛、神经性疼痛及其相关的过度疼痛和异常疼痛、糖尿病性神经病疼痛、灼痛、交感神经维持的疼痛、去神经综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、在呼吸、生殖泌尿、胃肠或血管区域的内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠病、胃溃疡、十二指肠溃疡、腹泻、由坏死性剂引起的胃部病变、毛发生长、血管运动性或过敏性鼻炎、支气管障碍或膀胱障碍。
• Substituent effects on the kinetics of reductively-initiated fragmentation of nitrobenzyl carbamates designed as triggers for bioreductive prodrugs
  作者：Michael P. Hay、Bridget M. Sykes、William A. Denny、Charmian J. O’Connor

  DOI：10.1039/a904067f

  日期：——

  evaluated as bioreductive drugs, there has been no systematic study of substituent effects on the rate of this fragmentation (which should be as fast as possible following reduction). We therefore prepared a series of 2-, 3- and α-substituted 4-[N-methyl-N-(4-nitrobenzyloxycarbonyl)amino]phenylacetamides as model compounds to study these effects. The majority of the carbamates were prepared by in situ formation

  4-硝基苄基氨基甲酸酯是引起生物还原性药物的诱因，特别是与E.coli B硝基还原酶联用，可有效地将它们还原为相应的羟胺。然后，它们会碎裂，释放出高毒性的胺基毒素。尽管许多4-硝基苄基氨基甲酸酯衍生物已被评估为生物还原药物，但尚未系统地研究取代基对这种断裂速率的影响（还原后应尽可能快）。因此，我们制备了一系列2-，3-和α-取代的4- [ N-甲基-N-（4-硝基苄氧基羰基）氨基]苯基乙酰胺作为模型化合物，以研究这些作用。大多数氨基甲酸酯是原位制备的形成适当的4-硝基苄醇的氯甲酸酯，并与4-（甲基氨基）苯基乙酸甲酯反应，然后进行酯水解和1,1'-羰基二咪唑（CDI）介导的与N，N-二甲基氨基乙胺的偶联。通过在磷酸盐缓冲的丙-2-醇水溶液中对硝基化合物进行60 Coγ射线辐照产生羟胺。将反应物用反相HPLC进行分析，以确定最大的半衰期（M吨1/2所产生的羟胺的），并从这些胺的释放后10个半衰
• Development of Bioreduction Labile Protecting Groups for the 2′-Hydroxyl Group of RNA
  作者：Hisao Saneyoshi、Kodai Nakamura、Kazuma Terasawa、Akira Ono

  DOI：10.1021/acs.orglett.0c02086

  日期：2020.8.7

  and deprotection of the 2′-hydroxyl group of RNAs are critical for RNA-based drug discovery. This paper reports development of a bioreduction labile protecting group of the 2′-hydroxyl group in RNA. After the reduction of the nitro group in a chemical or enzymatic manner, the protecting groups were removed spontaneously. The attachment of electron-donating groups to the benzene ring or benzylic carbon

  RNA 2'-羟基的保护和脱保护对于基于 RNA 的药物发现至关重要。本文报告了 RNA 中 2'-羟基的生物还原不稳定保护基团的开发。在以化学或酶促方式还原硝基后，保护基团自发去除。给电子基团与苯环或苄基碳的连接能够在生理条件下快速且可控地对 2'-羟基保护基进行脱保护。