N-(3,4-Dichlor-benzyloxy)-phthalimid | 38936-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3,4-Dichlor-benzyloxy)-phthalimid
• 英文别名: 2-(3,4-dichlorobenzyloxy)isoindole-1,3-dione；N-(3,4-dichloro-benzyloxy)-phthalimide；2-((3,4-Dichlorobenzyl)oxy)isoindoline-1,3-dione；2-[(3,4-dichlorophenyl)methoxy]isoindole-1,3-dione
• CAS: 38936-82-2
• 化学式: C₁₅H₉Cl₂NO₃
• 分子量: 322.147
• InChiKey: MFHSFGWIMQQPTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-Dichlor-benzyloxy)-phthalimid 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3,4-二氯苄氧胺盐酸盐
  参考文献：
  名称：

  来自烟酸的新型N- (芳基甲氧基)-2-氯烟酰胺的合成、晶体结构、除草活性和 SAR 研究

  摘要：

  烟酸又称烟酸，是一种天然产物，广泛存在于动植物中。为了发现基于天然产物的新型除草剂，设计并合成了一系列N- (芳基甲氧基)-2-氯代烟酰胺。一些新的N -(芳基甲氧基)-2-氯烟酰胺在 100 μM 时对Agrostis stolonifera（蓼蒿）表现出优异的除草活性。化合物5F（2-氯- ñ - （（3,4-二氯苄基）氧基）烟酰胺）具有优良的除草活性对青萍（浮萍），与IC 50值 7.8 μM，而商业除草剂异恶草酮和丙苯腈的值分别为 125 和 2 μM。本文报道的构效关系可用于开发抗单子叶杂草的新型除草剂。

  DOI：

  10.1021/acs.jafc.0c07538
• 作为产物：
  描述：

  2-(羟基氨基甲酰基)苯甲酸 在 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 N-(3,4-Dichlor-benzyloxy)-phthalimid
  参考文献：
  名称：

  来自烟酸的新型N- (芳基甲氧基)-2-氯烟酰胺的合成、晶体结构、除草活性和 SAR 研究

  摘要：

  烟酸又称烟酸，是一种天然产物，广泛存在于动植物中。为了发现基于天然产物的新型除草剂，设计并合成了一系列N- (芳基甲氧基)-2-氯代烟酰胺。一些新的N -(芳基甲氧基)-2-氯烟酰胺在 100 μM 时对Agrostis stolonifera（蓼蒿）表现出优异的除草活性。化合物5F（2-氯- ñ - （（3,4-二氯苄基）氧基）烟酰胺）具有优良的除草活性对青萍（浮萍），与IC 50值 7.8 μM，而商业除草剂异恶草酮和丙苯腈的值分别为 125 和 2 μM。本文报道的构效关系可用于开发抗单子叶杂草的新型除草剂。

  DOI：

  10.1021/acs.jafc.0c07538

文献信息

• Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
  作者：Ravikumar Akunuri、Vaishnavi Veerareddy、Grace Kaul、Abdul Akhir、Tanveer Unnissa、Ramulu Parupalli、Y.V. Madhavi、Sidharth Chopra、Srinivas Nanduri

  DOI：10.1016/j.bioorg.2021.105288

  日期：2021.11

  attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among

  由多重耐药菌引起的感染已成为对人类健康的持续威胁。尽管目前有多种抗生素可用于治疗传染病，但仍有大量细菌菌株对其中的许多菌株产生了抗药性。其中，金黄色葡萄球菌引起的感染在成人和儿童人群中占主导地位。吲哚是一种突出的化学支架，存在于许多具有药理活性的天然产品和合成药物中。许多含肟醚的化合物由于其有趣的生物学特性而引起了研究人员的关注。目前的工作详细介绍了含吲哚肟醚衍生物的合成及其对一组细菌和分枝杆菌菌株的抗菌活性的评估。合成的化合物对耐药性金黄色葡萄球菌表现出良好到中等的活性，包括对万古霉素的耐药性。其中，发现化合物5h对金黄色葡萄球菌的敏感菌株以及 MRSA 和 VRSA 菌株具有强效活性具有1μMIC克/毫升和2-4μ克/毫升分别。此外，发现化合物5h对 Vero 细胞无毒，并表现出>40 的良好选择性指数。此外，5h、E -9a和E -9b对金黄色葡萄球菌具有良好的生物膜抑制作用。有了这
• Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs
  作者：Ming-Zhong Wang、Han Xu、Tuan-Wei Liu、Qi Feng、Shu-Jing Yu、Su-Hua Wang、Zheng-Ming Li

  DOI：10.1016/j.ejmech.2011.01.031

  日期：2011.5

  A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by H-1 NMR, C-13 NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 mu g mL(-1). Compound 2a and 3a exhibited good activities against P. piricola at low dosage. (C) 2011 Elsevier Masson SAS. All rights reserved.
• O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1
  作者：William P. Malachowski、Maria Winters、James B. DuHadaway、Ariel Lewis-Ballester、Shorouk Badir、Jenny Wai、Maisha Rahman、Eesha Sheikh、Judith M. LaLonde、Syun-Ru Yeh、George C. Prendergast、Alexander J. Muller

  DOI：10.1016/j.ejmech.2015.12.028

  日期：2016.1

  Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a. potent sub-micromolar inhibitor of IDO1. Structure activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Catalytic <i>Ortho</i>-Acetoxylation of Masked Benzyl Alcohols via an <i>Exo</i>-Directing Mode
  作者：Zhi Ren、Jonathan E. Schulz、Guangbin Dong

  DOI：10.1021/acs.orglett.5b01098

  日期：2015.6.5

  A Pd-catalyzed ortho-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient exo-type directing group for arene (sp(2)) CH functionalization. Two strategies were demonstrated to remove the directing group through N-O and C-O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method.