1-[4-(3-氯丙氧基)-2-羟基苯基]乙酮 | 172739-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-(3-氯丙氧基)-2-羟基苯基]乙酮
• 英文名称: 1-<4-(3-chloropropoxy)-2-hydroxyphenyl>-1-ethanone
• 英文别名: [4-(3-chloropropoxy)-2-hydroxyphenyl]-1-ethanone；1-(4-(3-chloropropoxy)-2-hydroxyphenyl)ethanone；4'-(3-Chloropropoxy)-2'-hydroxyacetophenone；1-[4-(3-Chloropropoxy)-2-hydroxyphenyl]-1-ethanone；1-[4-(3-chloropropoxy)-2-hydroxyphenyl]ethanone
• CAS: 172739-45-6
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: KPADWTIRNNDRIY-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74°
• 沸点：
  388.2±27.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914700090
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  1-[4-(3-氯丙氧基)-2-羟基苯基]乙酮 在 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 阿巴哌酮
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics. 2. Pharmacological Profile of 7-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (Abaperidone, FI-8602)

  摘要：

  A series of novel 7-[3-(1-piperidinyl)propoxy]chromenones was synthesized and tested as potential antipsychotics in several in vitro and in vivo assays. The compounds possessed good affinity for Dp receptors, together with a greater affinity for 5-HT2 receptors, a profile which has been proposed as a model for atypical antipsychotics. Several agents also displayed a high potency in the climbing mice assay on oral administration, suggesting a potent antipsychotic effect as compared to reference standards. Compound 23 was selected for fur ther pharmacological evaluation. induction of catalepsy and inhibition of stereotypies weaker than standards, along with a lower increase in serum prolactin levels, were indicative of a potential atypical profile for this compound. From these results, 7-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (23, abaperidone) has been proposed for clinical evaluation in humans as a potential atypical antipsychotic.

  DOI：

  10.1021/jm9810396
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以93%的产率得到1-[4-(3-氯丙氧基)-2-羟基苯基]乙酮
  参考文献：
  名称：

  天然产物作为新型杀菌剂的来源（I）：苯乙酮衍生物对植物病原真菌的合成和抗真菌活性

  摘要：

  可以方便地合成几个带有各种烷基或苄基取代基的45种苯乙酮衍生物，并通过1 H和13 C NMR光谱，HRMS和单晶X射线分析对它们的结构进行表征。通过菌丝体生长速率测定法评估了它们对一组植物病原性真菌的体外抗真菌活性。在它们中，有12种衍生物（例如3a–c，4c和4e）对某些植物病原体表现出比作为阳性对照的商业杀菌剂氨甲唑更有效的抗真菌作用。特别是具有IC 50的化合物3b10–19μg/ mL的值被发现是该系列中最活跃的，可能是进一步优化的潜在先导结构。还讨论了一系列苯乙酮的初步结构-活性关系（SAR）研究。

  DOI：

  10.1111/cbdd.12064

文献信息

• 4-p-fluorobenzoyl-1-piperidinyl-propoxy-chromen-4-one derivatives, their
  申请人：Ferrer Internacional, S.A.

  公开号：US05643927A1

  公开（公告）日：1997-07-01

  The present invention relates to new chromene compounds of the general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, alkyl having from 1 to 4 carbon atoms, halogen, trifluoromethyl, optionally substituted phenyl, or hydroxymethyl, as well as their pharmaceutically acceptable addition salts. These compounds are useful in the treatment of psychosis and schizophrenia.

  本发明涉及一般式（I）的新的咔咯酮化合物：其中R₁和R₂为氢、具有1至4个碳原子的烷基、卤素、三氟甲基、可选取代的苯基或羟甲基，以及它们的药用可接受的加合物盐。这些化合物在治疗精神病和精神分裂症中有用。
• A new efficient synthesis of 3-(hydroxymethyl)-4<i>H</i>-chromen-4-ones
  作者：Jordi Bolós、Teresa Loscertales、Joan Nieto、Aurelio Sacristán、José A. Ortiz

  DOI：10.1002/jhet.5570370529

  日期：2000.9

  An efficient and versatile synthesis of variously substituted 3-(hydroxymethyl)-4H-chromen-4-ones is reported. The compounds are prepared by hydroxymethylation of the precursor 2-hydroxy-4-chromanones followed by acid dehydration.

  报道了各种取代的3-（羟甲基）-4 H-铬烯-4-酮的有效和通用的合成。通过将前体2-羟基-4-二氢呋喃酮进行羟甲基化，然后进行酸脱水来制备化合物。
• Novel aminothiazolyl-functionalized phosphonium ionic liquid as a scavenger for toxic metal ions from aqueous media; mining to useful antibiotic candidates
  作者：Nadiyah S. Alahmadi、Reda F.M. Elshaarawy

  DOI：10.1016/j.molliq.2019.01.154

  日期：2019.5

  successfully fabricated a new aminothiazolyl-functionalized phosphonium ionic liquid (HATPS) for HMIs (Ag(I), Cu(II), Zn(II), Fe(III)) scavenging applications. Moreover, the scavenging outputs were examined as new antibiotic candidates. The new scavenger exhibited excellent scavenging efficiency (up to 96% in the case of Ag(I) for an initial Ag(I) ions concentration of 0.03 M and at 0.03 M of scavenger dose)

  重金属离子（HMI）通过许多机制引起严重的毒性和致癌性，目前尚不清楚。因此，本文的目的是探索新的简单高效的HMI清道夫。在这一努力中，我们已经成功地制备了用于HMI（Ag（I），Cu（II），Zn（II），Fe（III））清除应用的新型氨基噻唑基官能化的磷化氢离子液体（HATPS）。此外，将清除产物作为新的抗生素候选物进行了检查。新的清除剂表现出出色的清除效率（对于初始Ag（I）离子浓度为0.03 M且清除剂剂量为0.03 M的情况，在Ag（I）的情况下可达96％），并且易于再生和重复使用。HATPS优于基于聚合物的清除剂，可归因于其简单性，实时监控和较短的反应时间。此外，HATPS有效地用作分光光度探针，用于测定水介质中的Fe（III）的LOD为0.322 ppm的Fe（III）。抗菌素调查显示，清除产物表现出中等至出色的广谱抗菌功效，并具有较好的抗药性。大肠杆菌药剂（MIC大肠杆菌 =
• 7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics
  作者：Jordi Bolós、Santiago Gubert、Lluís Anglada、Josep M. Planas、Carme Burgarolas、Josep M. Castelló、Aurelio Sacristán、José A. Ortiz

  DOI：10.1021/jm950894b

  日期：1996.1.1

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.
• Polyphosphonium-oligochitosans decorated with nanosilver as new prospective inhibitors for common human enteric viruses
  作者：Ahmed R. Sofy、Ahmed A. Hmed、Naglaa F. Abd El Haliem、Mohamed A.-E. Zein、Reda F.M. Elshaarawy

  DOI：10.1016/j.carbpol.2019.115261

  日期：2019.12

  The main objective of this work to explore new safe antiviral agents against hepatitis A virus (HAV), norovirus (NoV) and Coxsackievirus B4 (CoxB4) infections. In this context, we have successfully prepared new poly-quaternary phosphonium oligochitosans (PQPOC(1,2)) to use them as natural synergistic in-situ bioreductants of silver ions into nanosilver and stabilizing agent for these nanosilver to fabricate PQPOCs-AgNPs nano-biocomposites (NBC1,2). The antiviral performance of the PQPOCs and NBCs against FCV, HAV, and CoxB4 reflects great virucidal activities for NBCs as compared with PQPOCs with maximum viral reduction% (41.42, 80.62, and 84.04%) for NBC1 against FCV, HAV, and CoxB4, respectively. Furthermore, the antiviral activity of NBC1 is concentration- / pH-dependent where NBC1 acquired its maximum antiviral at [NBC1] = 200 mu L/mL and pH 4. Based upon these facts, we could attribute the enhanced virucidal efficacy of NBC1: (i) binding of AgNPs to the virions active sites. (ii) Electrostatic interaction between the positive brushes of PQPOC and negative targets of viruses. (iii) Inducing ribonuclease catalyzed by CS to degrade the viral RNA and consequently prevents its transcription and translation.