(4-甲氧基苯基)(2-甲基-1-苯并呋喃-3-基)甲酮 | 94541-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-甲氧基苯基)(2-甲基-1-苯并呋喃-3-基)甲酮
• 英文名称: 2-methyl-3-(4'-methoxybenzoyl)benzofuran
• 英文别名: 2-methyl-3-(4-methoxybenzoyl)benzofuran；(4-methoxy-phenyl)-(2-methyl-benzofuran-3-yl)-methanone；2-Methyl-3--benzofuran；3-(4-Methoxybenzoyl)-2-methylbenzofuran；(4-methoxyphenyl)-(2-methyl-1-benzofuran-3-yl)methanone
• CAS: 94541-06-7
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: YHTKTSKKNRXRKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (4-甲氧基苯基)(2-甲基-1-苯并呋喃-3-基)甲酮 在 sodium tetrahydroborate 、 吡啶盐酸盐 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  Synthesis and Preliminary Characterization of a Novel Antiarrhythmic Compound (KB130015) with an Improved Toxicity Profile Compared with Amiodarone

  摘要：

  Recent developments in antiarrhythmic therapy have indicated that the best approach to pharmacologically controlling supraventricular arrhythmias and life-threatening ventricular tachyarrhythmias is by prolonging cardiac repolarization rather than by blocking conduction. In this context, amiodarone has emerged as the most potent compound, but its universal use has been limited by its toxicity profile. There are data to suggest that an important component of amiodarones antiarrhythmic action might be mediated via inhibition of thyroid hormone action in the heart. Therefore, a new series of carboxymethoxybenzoyl and benzyl derivatives of benzofuran has been prepared and evaluated as thyroid hormone receptor antagonists. Within this series, 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran KB130015 (7) was found to reveal the most promising in vitro data. It inhibits the binding of I-125-T-3 to the human thyroid hormone receptors (hThR) alpha(1) and beta(1). T-3-Antagonism was confirmed in reporter cell assays employing CHOKl cells (Chinese hamster ovary cells) stably transfected with hThRalpha(1) or hThRbeta(1) and an alkaline phosphatase reporter gene downstream a thyroid response element. The derived IC50 values were 2.2 muM for hThRalpha(1) and 4.1 muM for hThRbeta(1). Compound 7 was selected for further characterization of chronic effects on ventricular papillary muscle by transmembrane electrophysiology after daily intraperitoneal injection of the ligand (40 mg/kg body weight) in guinea pigs. Compound 7 was found to prolong the action potential duration at 90% (APD(90)) repolarization time (219 +/- 22 ms, control: 186 +/- 9 ms, p < 0.01) without exhibiting any reverse-rate dependency of action in a manner similar to that of amiodarone. In general, preliminary tolerance experiments with 7 demonstrated an improved safety profile compared to that of amiodarone. In summary, 7 appears to be less toxic than amiodarone while maintaining its electrophysiologic properties consistent with antiarrhythmic activity. Its potential antiarrhythmic actions warrant further investigations.

  DOI：

  10.1021/jm001126+
• 作为产物：
  描述：

  1-((4-methoxyphenyl)ethynyl)-2-(vinyloxy)benzene 在 1,10-菲罗啉 、 氧气 、 iron(II) chloride 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以70%的产率得到(4-甲氧基苯基)(2-甲基-1-苯并呋喃-3-基)甲酮
  参考文献：
  名称：

  一种2-甲基-3-苯甲酰基苯并呋喃衍生物的制 备方法

  摘要：

  本发明公开了一种2‑甲基‑3‑苯甲酰基苯并呋喃衍生物的制备方法，该方法以1‑(苯基乙炔基)‑2‑(乙烯氧基)苯类取代物为原料，FeCl2为催化剂，Phen为配体，PMHS为还原剂，乙醇、异丙醇、正丁醇或叔丁醇为溶剂，在氧气气氛下，反应温度为60℃，反应12h，合成目标产物，该合成方法简单，条件温和，收率较高，具有良好的应用前景。

  公开号：

  CN108484546B

文献信息

• [EN] RECEPTOR LIGANDS
  申请人：KAROBIO AKTIEBOLAG

  公开号：WO1992020331A1

  公开（公告）日：1992-11-26

  (EN) Use of a compound selected from the group consisting of 3,5-diiodo-4-(2-N,N-diethylaminoethoxy)phenyl-(2-butylbenzofur-3-yl)methanol hydrochloride (001), 2-methyl-3-(3,5-diiodo-4-(2-N,N-diethylaminoethoxy)-benzoyl)benzofuran hydrochloride (003), 2-n-butyl-3-(3,5-diiodo-4-carboxymethoxybenzoyl)benzofuran (005), 2-methyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofuran (011), 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (015), 4'-hydroxy-3'-iodo-3,5-diiodo-4-(2-N,N-dimethylaminoethoxy)benzophenon hydrochloride (024), 2-butyl-3-(3-iodo-4-hydroxybenzoyl)benzofuran (029), 4',4-dihydroxy-3'3,5-triiodo-diphenylmethan (032), which compound is a 3,5,3'-triiodothyronine (T-3) receptor ligand, for the preparation of a medicament for the therapeutic or prophylactic treatment of a disorder which depends on the expression of T-3 regulated genes, and pharmaceutical preparations comprising said compounds, are disclosed. Further, a method of prophylactically or therapeutically treating a patient having a disorder which depends on the expression of 3,5,3'-triiodo-thyronine (T-3) regulated genes is also disclosed. The invention additionally comprises product protection for all the above listed compounds, except the compound (011).(FR) On décrit l'utilisation d'un composé choisi parmi le groupe suivant: hydrochlorure de 3,5-diiodo-4-(2-N,N-diéthylaminoéthoxy)phényl-(2-butylbenzofur-3-yl)méthanol (001); hydrochlorure de 2-méthyl-3-(3,5-diiodo-4-(2-N,N-diéthylaminoéthoxy)-benzoyl)benzofurane (003); 2-n-butyl-3-(3,5-diiodo-4-carboxyméthoxybenzoyl)benzofurane (005); 2-méthyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofurane (011); 2-méthyl-3-(3,5-diiodo-4-carboxyméthoxybenzyl)benzofurane (015); hydrochlorure de 4'-hydroxy-3'-iodo-3,5 diiodo-4-(2-N,N-diméthylaminoéthoxy)benzophénone (024); 2-butyl-3-(3-iodo-4-hydroxybenzoyl)benzofurane (029); 4',4-dihydroxy-3'3,5-triiodo-diphénylméthane (032), ledit composé étant un ligand de récepteur de 3,5,3'-triiodothyronine (T-3), servant à la préparation d'un médicament pour le traitement thérapeutique ou prophylactique d'une affection qui dépend de l'expression de gènes à régulation T-3, ainsi que des préparations pharmaceutiques renfermant lesdits composés. De plus, on décrit une méthode de traitement prophylactique ou thérapeutique d'un patient atteint d'une affection qui dépend de l'expression de gènes à régulation 3,5,3'-triiodo-thyronine (T-3). Les produits dont la protection est également demandée sont tous les composés énumérés ci-dessus, à l'exception du composé (011).

  使用从以下组中选择的化合物，包括3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯基-(2-丁基苯并呋喃-3-基)甲醇盐酸盐（001）、2-甲基-3-(3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯甲酰)苯并呋喃盐酸盐（003）、2-正丁基-3-(3,5-二碘-4-羧甲氧基苯甲酰)苯并呋喃（005）、2-甲基-3-(3,5-二碘-4-羟基苯甲酰)苯并呋喃（011）、2-甲基-3-(3,5-二碘-4-羧甲氧基苯基)苯并呋喃（015）、4'-羟基-3'-碘-3,5-二碘-4-(2-N,N-二甲基氨基乙氧基)苯基酮盐酸盐（024）、2-丁基-3-(3-碘-4-羟基苯甲酰)苯并呋喃（029）、4',4-二羟基-3'3,5-三碘-二苯甲烷（032），该化合物为3,5,3'-三碘甲状腺素（T-3）受体配体，用于制备治疗或预防依赖T-3调节基因表达的疾病的药物，以及包含该化合物的制药制剂。此外，还公开了一种预防性或治疗性治疗患有依赖3,5,3'-三碘甲状腺素（T-3）调节基因表达的疾病的患者的方法。该发明还包括对以上列出的所有化合物的产品保护，但不包括化合物（011）。
• Pharmaceutical compositions and methods of producing coronary
  申请人：Smith Kline

  公开号：US03975537A1

  公开（公告）日：1976-08-17

  Pharmaceutical compositions and methods of producing coronary vasodilation by administering substituted benzofurans, for example 2-n-butyl-3-[4' -(2-hydroxy-3-isopropylamino)propoxybenzoyl] benzofuran.

  通过给予取代苯并呋喃，例如2-正丁基-3-[4'-(2-羟基-3-异丙基氨基)丙氧基]苯并呋喃，制备药物组合物并进行冠状动脉扩张的方法。
• Certain 4-(3-azacycloalkoxy or azacycloalkylmethoxy)benzoylbenzofurans
  申请人：SmithKline Corporation

  公开号：US03983245A1

  公开（公告）日：1976-09-28

  The compounds of this invention are substituted benzofurans and benzothiophenes having pharmacological activity. In particular, these compounds have coronary vasodilator activity and are useful in the treatment of angina pectoris.

  这项发明的化合物是具有药理活性的取代苯并呋喃和苯并噻吩。特别地，这些化合物具有冠状动脉扩张剂活性，并且在治疗心绞痛方面是有用的。
• Receptor ligands
  申请人：Karobio Aktiebolag

  公开号：US05567728A1

  公开（公告）日：1996-10-22

  Use of a compound selected from the group consisting of 3,5-diiodo-4-(2-N, N-diethylaminoethoxy)phenyl-(2-butylbenzofur-3-yl)methanol hydrochloride (001), 2-methyl-3-(3,5-diiodo-4-(2-N,N-diethylaminoethoxy)-benzoyl)benzofuran hydrochloride (003), 2-n-butyl-3-(3,5-diiodo-4-carboxymethoxybenzoyl)benzofuran (005), 2-methyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofuran (011), 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (015), 4'-hydroxy-3'-iodo-3,5-diiodo-4-(2-N,N-diethylaminoethoxy)benzophenon hydrochloride (024), 2-butyl-3-(3-iodo-4-hydroxy-benzoyl)benzofuran (029), 4'4'-dihydroxy-3'3,5-triiododiphenylmethan (032), which compound is a 3,5,3'-triiodothyronine (T-3) receptor ligand, for the preparation of a medicament for the therapeutic or prophylactic treatment of a disorder which depends on the expression of T-3 regulated genes, and pharmaceutical preparations comprising said compounds, are disclosed. Further, a method of prophylactically or therapeutically treating a patient having a disorder which depends on the expression of 3,5,3"-triiodo-thyronine (T-3) regulated genes is also disclosed. The invention additionally comprises product protection for all the above listed compounds, except the compound (011).

  本发明揭示了选择自3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯基-(2-丁基苯并呋喃-3-基)甲醇盐酸盐(001)、2-甲基-3-(3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯甲酰)苯并呋喃盐酸盐(003)、2-丁基-3-(3,5-二碘-4-羧甲氧基苯甲酰)苯并呋喃(005)、2-甲基-3-(3,5-二碘-4-羟基苯甲酰)苯并呋喃(011)、2-甲基-3-(3,5-二碘-4-羧甲氧基苯甲基)苯并呋喃(015)、4'-羟基-3'-碘-3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯基酮盐酸盐(024)、2-丁基-3-(3-碘-4-羟基苯甲酰)苯并呋喃(029)、4'4'-二羟基-3'3,5-三碘二苯甲烷(032)中的一种化合物，该化合物是3,5,3'-三碘甲状腺素(T-3)受体配体，用于制备治疗或预防取决于T-3调节基因表达的疾病的药物，以及包含上述化合物的制药制剂。此外，本发明还揭示了一种预防性或治疗性治疗患有取决于3,5,3"-三碘甲状腺素(T-3)调节基因表达的疾病的患者的方法。该发明还包括所有上述列出的化合物的产品保护，但不包括化合物(011)。
• 3,5,3'-triiodothyronine receptor ligands
  申请人：——

  公开号：US05585404A1

  公开（公告）日：1996-12-17

  Use of a compound selected from the group consisting of 3,5-diiodo-4-(2-N,N-diethylaminoethoxy)phenyl-(2-butylbenzofur-3-yl)methan ol hydrochloride (001), 2-methyl-3-(3,5-diiodo-4-(2-N,N-diethylaminoethoxy)-benzoyl)benzofuran hydrochloride (003), 2-n-butyl-3-(3,5-diiodo-4-carboxymethoxybenzoyl)benzofuran (005), 2-methyl-3-(3,5-diiodo-4-hydroxy-benzoyl)benzofuran (011), 2-methyl-3-(3,5-diiodo-4-carboxymethoxybenzyl)benzofuran (015), 4'-hydroxy-3'-iodo-3,5-diiodo-4-(2-N,N-diethylaminoethoxy)benzophenon hydrochloride (024), 2-butyl-3-(3-iodo-4-hydroxybenzoyl)benzofuran (029), 4'4'-dihydroxy-3'3,5-triiododiphenylmethan (032), which compound is a 3,5,3'-triiodothyronine (T-3) receptor ligand, for the preparation of a medicament for the therapeutic or prophylactic treatment of a disorder which depends on the expression of T-3 regulated genes, and pharmaceutical preparations comprising said compounds, are disclosed. Further, a method of prophylactically or therapeutically treating a patient having a disorder which depends on the expression of 3,5,3"-triiodo-thyronine (T-3) regulated genes is also disclosed. The invention additionally comprises product protection for all the above listed compounds, except the compound (011).

  使用从以下组中选出的化合物，包括3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯基-(2-丁基苯并呋喃-3-基)甲醇盐酸盐(001)、2-甲基-3-(3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯酰基)苯并呋喃盐酸盐(003)、2-正丁基-3-(3,5-二碘-4-羧甲氧基苯酰基)苯并呋喃(005)、2-甲基-3-(3,5-二碘-4-羟基苯酰基)苯并呋喃(011)、2-甲基-3-(3,5-二碘-4-羧甲氧基苯基)苯并呋喃(015)、4'-羟基-3'-碘-3,5-二碘-4-(2-N,N-二乙基氨基乙氧基)苯基酮盐酸盐(024)、2-丁基-3-(3-碘-4-羟基苯酰基)苯并呋喃(029)、4'4'-二羟基-3'3,5-三碘二苯甲烷(032)，该化合物是3,5,3'-三碘甲状腺素(T-3)受体配体，用于制备治疗或预防依赖于T-3调节基因表达的疾病的药物和包含上述化合物的制剂。此外，还公开了一种预防性或治疗性治疗患有依赖于3,5,3''-三碘甲状腺素(T-3)调节基因表达的疾病的患者的方法。该发明还包括对所有上述列出的化合物的产品保护，除了化合物(011)。