(4-Bromobenzyl)phosphonsaeure-dichloride | 98273-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-Bromobenzyl)phosphonsaeure-dichloride
• 英文别名: [(4-Bromophenyl)methyl]phosphonic dichloride；1-bromo-4-(dichlorophosphorylmethyl)benzene
• CAS: 98273-58-6
• 化学式: C₇H₆BrCl₂OP
• 分子量: 287.908
• InChiKey: YBISNNUZDGFMEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘化胆碱 、 (4-Bromobenzyl)phosphonsaeure-dichloride 在 吡啶 作用下， 反应 72.0h， 以0.071 g的产率得到2-[(4-Bromophenyl)methyl-hydroxyphosphoryl]oxyethyl-trimethylazanium
  参考文献：
  名称：

  Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the Acanthocheilonema viteae Product ES-62 Prevents Development of Collagen-Induced Arthritis

  摘要：

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,

  DOI：

  10.1021/jm401251p
• 作为产物：
  描述：

  4-溴苄基亚磷酸二乙酯 在 盐酸 、 氯化亚砜 作用下， 以 水 为溶剂， 反应 68.0h， 生成 (4-Bromobenzyl)phosphonsaeure-dichloride
  参考文献：
  名称：

  Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the Acanthocheilonema viteae Product ES-62 Prevents Development of Collagen-Induced Arthritis

  摘要：

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,

  DOI：

  10.1021/jm401251p

文献信息

• Fünf- und sechsgliedrige cyclische Phosphonsäure-diamide und-thioester-amide sowie Spirobi[oxazaphosphole]
  作者：Richard Neidlein、Stephan Buseck

  DOI：10.1002/hlca.19920750806

  日期：1992.12.16

  Five- and Six-Membered Cyclic Phosphonic Diamides, Thioester-amides and Spirobi[oxazaphospholes]

  五元和六元环磷酰胺，硫酯酰胺和螺环[恶唑磷]
• Creating Pyrethrin Mimetic Phosphonates as Chemical Genetics Tools Targeting the GDSL Esterase/Lipase TcGLIP to Investigate Pyrethrin Biosynthesis
  作者：Noritada Matsuo、Yukimi Sugisaka、Shiori Aoyama、Makoto Ihara、Harue Shinoyama、Munetaka Hosokawa、Yoshinobu Kamakura、Daisuke Tanaka、Yoo Tanabe、Kazuhiko Matsuda

  DOI：10.1021/acs.jmedchem.3c00285

  日期：2023.6.22

  biosynthesis. The compounds were synthesized by reacting mono-alkyl or mono-benzyl-substituted phosphonic dichloride with pyrethrolone, the alcohol moiety of pyrethrin I and II, and then p-nitrophenol. n-Pentyl (C5) and n-octyl (C8)-substituted compounds were the most potent of the (S)p,(S)c, and (R)p,(S)c diastereomers, respectively. The (S)-pyrethrolonyl group is more effective than the (R)-pyrethrolonyl

  菊叶中的除虫菊酯是天然杀虫剂，对传播疾病的蚊子等飞行昆虫具有高击倒和杀灭活性。尽管对除虫菊酯的需求不断增加，但除虫菊酯生物合成的机制仍然难以捉摸。为了阐明这一点，我们首次创建了针对支持除虫菊酯生物合成的 GDSL 酯酶/脂肪酶（GELP 或 TcGLIP）的除虫菊酯模拟膦酸盐。该化合物是通过单烷基或单苄基取代的二氯膦与吡虫啉、除虫菊酯I和II的醇部分以及对硝基苯酚反应合成的。正戊基 (C5) 和正辛基 (C8) 取代的化合物是最有效的 ( S) p ,( S ) c和( R ) p ,( S ) c非对映体。( S )-拟除虫菊基基团在阻断 TcGLIP 方面比 ( R )-拟除虫菊基基团更有效，与 ( S ) p、( S ) c -C5 和 ( R ) p复合的 TcGLIP 模型预测的特征一致， ( S ) c -C8 探针。( S ) p ,( S ) c-C5 化合物抑制了T. c
• Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the <i>Acanthocheilonema viteae</i> Product ES-62 Prevents Development of Collagen-Induced Arthritis
  作者：Lamyaa Al-Riyami、Miguel A. Pineda、Justyna Rzepecka、Judith K. Huggan、Abedawn I. Khalaf、Colin J. Suckling、Fraser J. Scott、David T. Rodgers、Margaret M. Harnett、William Harnett

  DOI：10.1021/jm401251p

  日期：2013.12.27

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,