2,3-dichloro-4'-methoxybutyrophenone | 41715-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dichloro-4'-methoxybutyrophenone
• 英文别名: 2',3'-dichloro-4'-methoxybutyrophenone；2',3'-Dichlor-4'-methoxy-butyrophenon；2',3'-Dichlor-4'-methoxybutyrophenon；2,3-Dichlor-4-methoxybutyrophenon；1-Butanone, 1-(2,3-dichloro-4-methoxyphenyl)-；1-(2,3-dichloro-4-methoxyphenyl)butan-1-one
• CAS: 41715-70-2
• 化学式: C₁₁H₁₂Cl₂O₂
• 分子量: 247.121
• InChiKey: NLWYCNCBSFKVBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-4'-methoxybutyrophenone 在 sodium hydroxide 、 苯甲醛 作用下， 以 乙醇 为溶剂， 生成 2,3-Dichloro-4-(2-benzylidenebutyryl)anisole
  参考文献：
  名称：

  [1-Hydroxy-5-indanyloxy (or thio)]-alkanoic acids

  摘要：

  揭示了1-羟基-5-茚氧（或硫）烷酸及其盐、酯和酰胺。这些产品在药用上具有双重作用，表现出利尿、排钠和降尿酸活性。这些酸产品可以通过几种合成方法制备。

  公开号：

  US04012524A1
• 作为产物：
  描述：

  2,3-二氯茴香醚 、 丁酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以90%的产率得到2,3-dichloro-4'-methoxybutyrophenone
  参考文献：
  名称：

  Agents for the treatment of brain edema. 2. [(2,3,9,9a-Tetrahydro-3-oxo-9a-substituted-1H-fluoren-7-yl)oxy]alkanoic acids and some of their analogs

  摘要：

  Our initial paper discussed brain edema resulting from traumatic head injury and the need for specific and effective agents to treat the disorder and disclosed a novel approach for the discovery of a drug of this kind. The current study describes the synthesis of a series of [(2,3,9,9a-tetrahydro-3-oxo-9a-substituted-1H-fluoren-7-yl)oxy]alk anoic acids and their analogues. These compounds were evaluated in an in vitro cerebrocortical tissue slice assay for their relative potencies in inhibiting K+ + HCO3- induced swelling. Structural modification at a number of sites in the "lead" compound revealed that significant biological activity was inherent only within a very narrow range of structural types. The observation that nearly all the biological activity resided in one of the two enantiomers demonstrated the marked stereospecificity of the most active compounds. One of the most potent compounds, (R)-(+)-[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren -7-yl) oxy]acetic acid ((+)-5c), exhibited a dose-response relationship in the in vivo acceleration/deceleration brain edema assay, and the data from the two highest doses were statistically significant. Electron microscopic examination demonstrated that the perivascular astroglial swelling that arises from this procedure is abolished in the animals treated with (+)-5c. This compound is currently being evaluated for its clinical efficacy and safety in the treatment of traumatic head injury.

  DOI：

  10.1021/jm00155a038

文献信息

• 一种二芳香烃取代丙烯酮类化合物及制备方法与应用
  申请人：山东大学

  公开号：CN109748785A

  公开（公告）日：2019-05-14

  本发明公开了一种二芳香烃取代丙烯酮类化合物及制备方法与应用，其结构式如式(Ⅰ)所示：其中A为B为氢、甲基或乙基；C为取代苯环、吡啶及呋喃杂环、2‑吡啶基、3‑吡啶基、4‑吡啶基、5‑1H‑吲哚基、4‑(N,N‑二甲胺基)苯基、4‑(N‑吡咯基)苯基、4‑[1‑(N–甲基哌嗪基)]苯基或4‑(1‑吗啉基)苯基。本发明的化合物具有结构新颖，对MCL细胞具有抑制活性效果、安全性高、制备成本低廉等优势，可以作为MCL很有前景的药物。
• 1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids
  申请人：Merck & Co., Inc.

  公开号：US03984465A1

  公开（公告）日：1976-10-05

  1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 2,2-disubstituted-5-hydroxy(or mercapto)-1-indanone with an haloalkanoic acid or ester thereof and, if the ester is employed, hydrolyzing the ester.

  披露了1-氧代-2,2-二取代-5-茚氧基（或硫代）脂肪酸及其盐、酯、酸酐、酰胺和5-四唑基衍生物。该产品具有双重药用功能，表现出利尿、盐利和尿酸排泄活性。通过将2,2-二取代-5-羟基（或巯基）-1-茚酮与卤代脂肪酸或其酯进行处理，并在使用酯时水解酯来制备酸产品。
• [1-Oxo-2-halo(or hydrogen) indanyloxy]-alkanoic acid
  申请人：Merck & Co., Inc.

  公开号：US04070539A1

  公开（公告）日：1978-01-24

  [1-Oxo-2-halo(or hydrogen)indanyloxy(or thio)]-alkanoic acid products and salts, esters and amide derivatives where the indanyl ring may be further substituted with from 2 to 5 nuclear substituents. The [1-oxo-2-haloindanyloxy-(or thio)]alkanoic acids are prepared (1) via the halogenation of a [1-oxoindanyloxy(or thio)]alkanoic acid or (2) via the addition of halogen to a [1-oxoindenyloxy(or thio)]-alkanoic acid. The [1-oxoindanyloxy(or thio)]alkanoic acids are prepared (1) via cyclialkylation of a (2-alkylideneacyl)-phenoxy(or thio)alkanoic acid or (2) via etherification of a hydroxy(or mercapto)-2-alkyl-1-indanone. The [1-oxo-2-halo(or hydrogen)indanyloxy(or thio)]alkanoic acids are diuretics and saluretics. In addition, some of these compounds are also able to maintain the uric acid concentration in the body at pretreatment level or to cause a decrease in uric acid concentration.

  [1-氧代-2-卤代(或氢)吲哚氧(或硫)基]-脂肪酸产物及其盐、酯和酰胺衍生物，其中吲哚环上可能进一步取代2-5个核取代基团。[1-氧代-2-卤代吲哚氧(或硫)基]-脂肪酸可通过以下方法制备：(1)将[1-氧代吲哚氧(或硫)基]-脂肪酸卤化或(2)将卤素添加到[1-氧代茚氧(或硫)基]-脂肪酸中。[1-氧代吲哚氧(或硫)基]-脂肪酸可通过以下方法制备：(1)将(2-烷基亚酰基)-苯氧(或硫)基脂肪酸環化或(2)将羟基(或巯基)-2-烷基-1-茚酮醚化。[1-氧代-2-卤代(或氢)吲哚氧(或硫)基]-脂肪酸具有利尿和盐利尿作用。此外，其中一些化合物还能够维持体内尿酸浓度在治疗前的水平或引起尿酸浓度下降。
• 1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkano acids
  申请人：Merck & Co., Inc.

  公开号：US04081554A1

  公开（公告）日：1978-03-28

  1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 2,2-disubstituted-5-hydroxy(or mercapto)-1-indanone with an haloalkanoic acid or ester thereof and, if the ester is employed, hydrolyzing the ester.

  本发明揭示了1-氧代-2,2-二取代-5-吲哚氧（或硫）代烷酸及其盐、酯、酐、酰胺和5-四唑基衍生物。这些产物具有双重药用价值，因为它们表现出利尿、排盐和尿酸排泄活性。酸类产物是通过将2,2-二取代-5-羟基（或巯基）-1-吲哚酮与卤代烷酸或其酯进行处理，并且如果使用酯，则水解酯来制备的。
• Development of a new experimental NMR strategy for covalent cysteine protease inhibitors screening: toward enhanced drug discovery
  作者：Abdelali Chihab、Nabil El Brahmi、Ghanem Hamdoun、Abdelmoula El Abbouchi、Hamza Ghammaz、Nadia Touil、Mostafa Bousmina、Elmostafa El Fahime、Saïd El Kazzouli

  DOI：10.1039/d4ra04938a

  日期：——

  targets. Cysteine proteases, also known as thiol proteases, catalyze the degradation of proteins by cleaving peptide bonds using the nucleophilic thiol group of cysteine. As part of our research, we are examining how cysteine, an essential amino acid found in the active site of the main protease (Mpro) enzyme in SARS-CoV-2, interacts with electrophilic groups present in ethacrynic acid (EA) and compounds

  在抗病毒药物的开发中，蛋白酶和聚合酶是最重要的靶标之一。半胱氨酸蛋白酶，也称为硫醇蛋白酶，通过使用半胱氨酸的亲核硫醇基团裂解肽键来催化蛋白质的降解。作为我们研究的一部分，我们正在研究半胱氨酸（一种存在于 SARS-CoV-2 主要蛋白酶 (M pro ) 活性位点的必需氨基酸）如何与利尿酸 ( EA ) 和化合物中存在的亲电子基团相互作用4、6和8形成硫-碳键。核磁共振（NMR）光谱用于监测半胱氨酸和迈克尔受体之间的反应速率。我们发现这些化合物对 M pro的抑制活性与其对半胱氨酸的化学反应性相关。这种方法可以作为药物开发中检测 M pro和其他半胱氨酸蛋白酶的潜在共价抑制剂的有价值的工具。