3-methyl-2-oxobutyl-triphenyl arsonium bromide | 121077-68-7

• 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: 3-methyl-2-oxobutyl-triphenyl arsonium bromide
• 英文别名: Arsonium, (3-methyl-2-oxobutyl)triphenyl-, bromide；(3-methyl-2-oxobutyl)-triphenylarsanium;bromide
• CAS: 121077-68-7
• 化学式: Br*C₂₃H₂₄AsO
• 分子量: 471.269
• InChiKey: MKSKITNZZYUEIK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-2-oxobutyl-triphenyl arsonium bromide 在 5percent Pd/BaSO₄ sodium hydroxide 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 20.0 ℃ 、220.64 kPa 条件下， 反应 47.33h， 生成 4-hydroxy-2-[2-(1H-indol-3-yl)ethyl]-2-propan-2-yl-3H-pyran-6-one
  参考文献：
  名称：

  4-Hydroxy-5,6-dihydropyrones as Inhibitors of HIV Protease:  The Effect of Heterocyclic Substituents at C-6 on Antiviral Potency and Pharmacokinetic Parameters

  摘要：

  Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, we previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029, 1) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable backup candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocyle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymatic and cellular tests) and-low cellular toxicity; furthermore, several analogues exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailabilty was (S)-3-(2-tertbutyl-4-hydroxymethy1- 5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (13-(S)). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, compound 13-(S) was chosen for further preclinical evaluation.

  DOI：

  10.1021/jm0003844
• 作为产物：
  描述：

  三苯胂 、 1-溴-3-甲基-2-丁酮 以 苯 为溶剂， 反应 6.0h， 以86%的产率得到3-methyl-2-oxobutyl-triphenyl arsonium bromide
  参考文献：
  名称：

  An Efficient and Stereoselective Synthesis of (E)-α-Enones via Arsonium Salts. Preparation of Key Intermediates for the Synthesis of Brassinosteroid and Prostaglandin

  摘要：

  (E)-1-烯基烷基酮[(E)-α-烯酮]通过(2-氧代烷基)三苯基砷溴化物与醛在固-液相转移条件下反应制备，具有高产率和高立体选择性。本文还报道了将这种方法应用于制备植物激素油菜素内酯和前列腺素PGF2α的关键中间体。

  DOI：

  10.1055/s-1988-27772

文献信息

• Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry.
  作者：Naoko Morisaki、Hisayoshi Kobayashi、Yumiko Yamamura、Masuo Morisaki、Kazuo Nagasawa、Yuichi Hashimoto

  DOI：10.1248/cpb.50.935

  日期：——

  Steroidal allylic alcohols formed Na+ adduct ion peaks [M+Na]+ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na+. The adduct ion was stable and did not undergo dehydroxylation

  在FAB质谱法中，通过添加NaCl，甾体烯丙醇形成Na +加成离子峰[M + Na] +。烯丙基醇与相应的饱和醇和烯烃的加合离子峰强度的比较表明，烯烃双键和近端羟基已与Na +配位。加合物离子是稳定的并且没有经历脱羟基。我们认为，Na +加合物可用于在FAB质谱条件下易于脱羟基的烯丙醇的分子量测定。还研究了α，β-不饱和羰基化合物的Na +加成离子。
• HIV protease inhibitors
  申请人：——

  公开号：US20040106606A1

  公开（公告）日：2004-06-03

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.

  本发明涉及一种新颖的具有改进药理学性质的带有连接杂环的二氢吡喃并具有强烈抑制HIV天冬氨酸蛋白酶以阻止HIV感染性的药物。这些二氢吡喃可用于开发治疗病毒感染和疾病，包括艾滋病的治疗方案。本发明还涉及二氢吡喃的合成方法以及用于制备最终化合物的中间体。
• Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol
  作者：JianGuo Cui、LongMei Zeng、JingYu Su、WeiGang Lu

  DOI：10.1016/s0039-128x(00)00132-x

  日期：2001.1

  Starting from stigmasterol (2), 24-methylenecholest-4-en-3 beta ,6 beta -diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3 beta -acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3 beta, 6 beta -diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). (C) 2001 Elsevier Science Inc. All rights reserved.
• Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol
  作者：Jian Guo Cui、Cui Wu Lin、Long Mei Zeng、Jing Yu Su

  DOI：10.1016/s0039-128x(02)00059-4

  日期：2002.12

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.
• Hazra, Braja G.; Kumar, Tirunahari Pavan; Pore, Vandana S., Journal of Chemical Research - Part S, 1996, # 12, p. 536 - 537
  作者：Hazra, Braja G.、Kumar, Tirunahari Pavan、Pore, Vandana S.

  DOI：——

  日期：——