3-氯-1-(2,4-二氯苯基)丙烷-1-酮 | 58631-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氯-1-(2,4-二氯苯基)丙烷-1-酮
• 英文名称: 3-chloro-1-(2,4-dichlorophenyl)propanone
• 英文别名: 3-chloro-1-(2,4-dichlorophenyl)propan-1-one；3-Chlor-1-(2,4-dichlorphenyl)-1-propanon；1-(2,4-dichlorophenyl)-3-chloropropanone
• CAS: 58631-66-6
• 化学式: C₉H₇Cl₃O
• 分子量: 237.513
• InChiKey: DHHKPBCMQRWSHN-UHFFFAOYSA-N

物化性质

• 沸点：
  125 °C(Press: 0.000001 Torr)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-氯-1-(2,4-二氯苯基)丙烷-1-酮 在 三乙胺 作用下， 以 xylene 、 苯 为溶剂， 反应 1.0h， 生成 2-(2,4-Dichloro-phenyl)-4-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-butan-2-ol; hydrochloride
  参考文献：
  名称：

  苄基哌嗪衍生物。I.1-（2，3，4-三甲氧基苄基）哌嗪衍生物的合成和生物学活性。

  摘要：

  合成了一系列1-（2, 3, 4-三甲氧基苄基）哌嗪（曲美他嗪）衍生物，并测试其脑血管扩张活性。几乎所有化合物的活性均强于曲美他嗪，其中γ-氨基三级醇6e-j表现出强大的脑血管扩张活性，优于辛那利嗪和罂粟碱。此外，这些化合物对椎动脉具有选择性的扩张作用。

  DOI：

  10.1248/cpb.35.2774
• 作为产物：
  描述：

  1-(2,4-二氯苯基)-3-羟基丙酮 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到3-氯-1-(2,4-二氯苯基)丙烷-1-酮
  参考文献：
  名称：

  1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies

  摘要：

  New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.

  DOI：

  10.1021/jm800009r

文献信息

• Benzylpiperazine derivatives. II. Syntheses and cerebral vasodilating activities of 1-((3-alkyl-3-hydroxy-3-phenyl)propyl)-4-benzylpiperazine derivatives.
  作者：HIROSHI OHTAKA、YOSHIAKI FUJIMOTO、KENJI YOSHIDA、TOSHIRO KANAZAWA、KEIZO ITO、GORO TSUKAMOTO

  DOI：10.1248/cpb.35.2782

  日期：——

  Analogs of 1-[ (3-alkyl-3-hydroxy-3-phenyl) propyl]-4- (2, 3, 4-trimethoxybenzyl) piperazine (1) were prepared and tested for cerebral vasodilating activity. It was found that the potency depends positively on the number of methoxyl groups on the benzyl moiety, and the homopiperazine analogs seem to be equipotent to the corresponding piperazines. From the standpoints of potency and ease of synthesis, 8k was selected for further study. Further analogs, which have various substituents in place of the benzyl moiety of 8k, were prepared and tested for cerebral vasodilating activity. These analogs were less potent than 8k. It was suggested that the benzyl moiety of 8k plays an important role in the high cerebral vasodilating activity.

  1-[ (3-烷基-3-羟基-3-苯基)丙基]-4- (2, 3, 4-三甲氧基苯基)哌嗪（1）的类似物被制备并测试了其脑血管扩张活性。研究发现，活性强度与苄基部分上的甲氧基团数量呈正相关，而同脉哌嗪类的类似物似乎与相应的哌嗪类同样具有活性。从活性和合成简便性来看，选定了8k进行进一步研究。随后制备了在8k的苄基部分替换为各种取代基的其他类似物，并测试了其脑血管扩张活性。这些类似物的活性均低于8k。研究者认为，8k的苄基部分在其高脑血管扩张活性中起着重要作用。
• Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation
  作者：Francesco Calzaferri、Paloma Narros-Fernández、Ricardo de Pascual、Antonio M.G. de Diego、Annette Nicke、Javier Egea、Antonio G. García、Cristóbal de los Ríos

  DOI：10.1021/acs.jmedchem.0c02145

  日期：2021.2.25

  Several P2X7 antagonists have been developed, though none of them reached clinical trials for this indication. In this work, we designed and synthesized novel blood–brain barrier (BBB)-permeable derivatives as potential P2X7 antagonists. They comprise purine or xanthine cores linked to an aryl group through different short spacers. Compounds were tested in YO-PRO-1 uptake assays and intracellular calcium

  ATP 门控 P2X7 嘌呤能受体 (P2X7) 参与许多神经退行性疾病 (NDD) 的发病机制。已经开发了几种 P2X7 拮抗剂，但没有一种达到该适应症的临床试验。在这项工作中，我们设计并合成了新型血脑屏障（BBB）渗透性衍生物作为潜在的 P2X7 拮抗剂。它们包含通过不同的短间隔基与芳基连接的嘌呤或黄嘌呤核心。在表达人 P2X7 的 HEK293 细胞系中的 YO-PRO-1 摄取测定和细胞内钙动力学、非洲爪蟾卵母细胞中的两电极电压钳记录以及小鼠腹膜巨噬细胞中的白细胞介素 1β 释放测定中测试了化合物。通过平行人工膜渗透性测定和 P-糖蛋白 ATP 酶活性评估 BBB 渗透性。二氯芳基嘌呤基乙醇具有一定的 P2X7 阻断作用，为化合物6 (2-(6-氯-9 H-嘌呤-9-基)-1-(2,4-二氯苯基)乙烷-1-酮)，命名为 ITH15004，是最有效的，选择性且 BBB 通透性拮抗剂。
• [EN] 4-MEMBERED RING CARBOXAMIDES USED AS NEMATICIDES<br/>[FR] CARBOXAMIDES PRÉSENTANT DES CYCLES À 4 CHAÎNONS UTILISÉS COMME NÉMATICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2015003951A1

  公开（公告）日：2015-01-15

  Compounds of the formula (I), in which the substituents are as defined in claim 1, are suitable for use as nematicides.

  式（I）中的化合物，其中取代基如权利要求1中定义的那样，适用于作为线虫杀虫剂。
• 4-MEMBERED RING CARBOXAMIDES USED AS NEMATICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：US20160157485A1

  公开（公告）日：2016-06-09

  Compounds of the formula (I), in which the substituents are as defined in claim 1 , are suitable for use as nematicides.

  公式(I)的化合物，其中取代基的定义如权利要求书1所述，适用于用作线虫灭除剂。
• Isoxazole anthelmintics
  作者：John B. Carr、Harry G. Durham、D. Kendall Hass

  DOI：10.1021/jm00217a014

  日期：1977.7

  A series of 3-halo-5-phenyl- and 3-phenyl-5-haloisoxazoles has demonstrated anthelmintic activity at doses ranging from 16 to 500 mg/kg orally against the rat roundworm, Nippostrongylus braziliensis. In the 5-phenyl series a halogen at the 3 position of the isoxazole ring was required for activity. However, in the 3-phenyl series activity was maintained after replacement of the 5-halogen with certain alkoxyl, thioalkoxyl, or amino groups. The 3-phenyl and 5-phenyl series apparently are not acting biologically at a common receptor site. Synthetic methods and structure-activity relationships are discussed.