3,4-二氯苄氧胺盐酸盐 | 84772-12-3

• 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: 3,4-二氯苄氧胺盐酸盐
• 中文别名: O-(3,4-二氯苄基)羟胺盐酸盐
• 英文名称: 3,4-Dichlor-benzyloxyamin
• 英文别名: O-(3,4-dichlorobenzyl)hydroxylamine；O-[(3,4-dichlorophenyl)methyl]hydroxylamine
• CAS: 84772-12-3
• 化学式: C₇H₇Cl₂NO
• 分子量: 192.045
• InChiKey: OVMBDDNTFJQHST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二氯苄氧胺盐酸盐 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 3,4-二氯苄氧胺盐酸盐
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.12.028
• 作为产物：
  描述：

  3,4-二氯氯苄 在 N-羟基氨基甲酸乙酯 、 sodium ethanolate 、 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到3,4-二氯苄氧胺盐酸盐
  参考文献：
  名称：

  人类组成型雄烷受体激动剂CITCO的立体异构化

  摘要：

  CITCO（6-（4-氯苯基）咪唑并[2,1- b ] [1,3]噻唑-5-甲醛-O-（3,4-二氯苄基）肟）是人类组成型雄甾烷受体的广泛激动剂（hCAR），一种具有新兴治疗适应症的关键肝异种传感器蛋白。为了解决CITCO的不足稳定性，限制其治疗潜力，合成了CITCO的E-和Z-异构体，并通过X射线晶体学，一维和二维NMR光谱进行了表征。发现这两种异构体在溶液中可能通过质子旋转机制在时间和浓度上进行E / Z异构化。我们的分子建模研究表明，两种立体异构体均可与hCAR结合。

  DOI：

  10.1016/j.tet.2020.131886

文献信息

• Transformation of masked benzyl alcohols to o-aminobenzaldehydes through C–H activation: a facile approach to quinazolines
  作者：Xiaolan Chen、Jian Han、Yan Zhu、Chunchen Yuan、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1039/c6cc05560e

  日期：——

  Direct Transformation of directing group to important synthetic units would provide a high atom efficiency synthetic approach in synthetic chemistry. Herein, a convenient protocol in synthesis of o-aminobenzaldehyde and benzoxazole...

  指导基团直接转化为重要的合成单元将为合成化学提供一种高原子效率的合成方法。此处是合成邻氨基苯甲醛和苯并恶唑的便捷方法...
• Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel <i>N</i>-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid
  作者：Chen-Sheng Yu、Qiao Wang、Joanna Bajsa-Hirschel、Charles L. Cantrell、Stephen O. Duke、Xing-Hai Liu

  DOI：10.1021/acs.jafc.0c07538

  日期：2021.6.16

  animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata

  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。
• Design and Synthesis of Terephthalic Acid‐Based Histone Deacetylase Inhibitors with Dual‐Stage Anti‐<i>Plasmodium</i>Activity
  作者：Katharina Stenzel、Ming Jang Chua、Sandra Duffy、Yevgeniya Antonova‐Koch、Stephan Meister、Alexandra Hamacher、Matthias U. Kassack、Elizabeth Winzeler、Vicky M. Avery、Thomas Kurz、Katherine T. Andrews、Finn K. Hansen

  DOI：10.1002/cmdc.201700360

  日期：2017.10.9

  work we aimed to develop parasite‐selective histone deacetylase inhibitors (HDAC) inhibitors with activity against the disease‐causing asexual blood stages of Plasmodium as well as causal prophylactic and/or transmission blocking properties. We report the design, synthesis, and biological testing of a series of 13 terephthalic acid‐based HDAC inhibitors. All compounds showed low cytotoxicity against

  在这项工作中，我们旨在开发具有选择性的寄生虫选择性组蛋白脱乙酰基酶抑制剂（HDAC）抑制剂，该抑制剂对引起疾病的无性疟原虫血液阶段具有活性，并具有因果预防和/或传播阻断特性。我们报告了一系列13种基于对苯二甲酸的HDAC抑制剂的设计，合成和生物学测试。所有化合物显示出对人胚胎肾（HEK293）细胞的细胞毒性低（IC 50：8-> 51μ米）中，用11还具有亚微摩尔的体外活性对药物敏感（3D7）和多药耐药（DD2）无性血液阶段的恶性疟原虫寄生虫（IC 50 ≈0.1-0.5μ米）。检查了一部分化合物对早期和晚期恶性疟原虫配子细胞和伯氏疟原虫外红细胞阶段寄生虫的活性。虽然仅观察到对配子细胞的中等活性（IC 50 > 2μm），但活性最高的化合物（N 1 -（（3,5-二甲基苄基）氧基）N 4-羟基对苯二甲酰胺1 f）表现出对微配子的亚微摩尔活性。伯氏疟原虫红细胞外阶段（IC 50 0.18μ米为比HepG2细胞红细胞外的形式）和>
• BACTERIOSTATS: III. OXYAMINES AND THEIR DERIVATIVES
  作者：A. F. McKay、D. L. Garmaise、G. Y. Paris、S. Gelblum

  DOI：10.1139/v60-050

  日期：1960.3.1

  A number of benzyloxyamines were prepared for conversion into urea and thiourea derivatives. The benzyloxyamine hydrochlorides on treatment with phosgene gave a mixture of the corresponding benzyl 4-(benzyloxy)-allophanate and benzyloxycarbamyl chloride. Triethylamine converted the benzyloxycarbamyl chlorides into the corresponding 1,3,5-tri-(benzyloxy)-isocyanuric acids. The reactions of the allophanates with amines and sodium hydroxide are described.

  为合成脲和硫脲衍生物，制备了一系列苄氧胺。苄氧胺盐酸盐与光气处理后生成相应的苄基4-(苄氧基)-异尿酸酯和苄氧基氨基甲酰氯的混合物。三乙胺将苄氧基氨基甲酰氯转化为相应的1,3,5-三-(苄氧基)-异氰酸酸。描述了异尿酸酯与胺和氢氧化钠的反应。
• 17-HYDROXY-17-PENTAFLUOROETHYL-ESTRA-4,9(10)-DIENE-11-ETHYNYLPHENYL DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AND USE THEREOF FOR TREATING DISEASES
  申请人：Klar Ulrich

  公开号：US20120190660A1

  公开（公告）日：2012-07-26

  The invention relates to 17-hydroxy-17-pentafluoroethylestra-4,9(10)-diene 11-ethynylphenyl derivatives of the formula I, in which R 1 and X are each as defined in the claims and the description, and to a process for preparation thereof and to the use thereof as medicaments.

  该发明涉及式I中的17-羟基-17-五氟乙基雌二烯-4,9(10)-二烯-11-乙炔基苯基衍生物，其中R1和X如索赔和描述中所定义，以及其制备方法和用作药物的用途。