Ethyl 2-(3-bromophenyl)-3-oxopropanoate | 681860-30-0

• 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: Ethyl 2-(3-bromophenyl)-3-oxopropanoate
• 英文别名: ethyl 2-(3-bromophenyl)-3-oxopropanoate
• CAS: 681860-30-0
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: BNYXCUYTAHGECY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(3-bromophenyl)-3-oxopropanoate 以 二苯醚 、 联苯 、 甲苯 为溶剂， 反应 20.0h， 生成 3-(3-bromophenyl)-5,7-dimethoxyquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047
• 作为产物：
  描述：

  3-溴苯乙酸乙酯 、 甲酸乙酯 在 sodium hydride 作用下， 以 乙醚 、 mineral oil 为溶剂， 反应 4.0h， 生成 Ethyl 2-(3-bromophenyl)-3-oxopropanoate
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047

文献信息

• [EN] SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL USES THEREOF<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET UTILISATIONS PHARMACEUTIQUES DE CEUX-CI
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2010127440A1

  公开（公告）日：2010-11-11

  The present invention relates to substituted aromatic compounds of Formula (I) and their pharmaceutical uses. Particular aspects of the invention relate to the use of those compounds in the prevention and/or treatment of various diseases and conditions in subjects, including the prevention or treatment of (i) blood disorders, (ii) renal disorders, nephropathies, or renal disorder complications; (iii) inflammatory-related diseases; and/or (iv) oxidative stress related disorders.

  本发明涉及式(I)的取代芳香化合物及其医药用途。发明的特定方面涉及在受试者中预防或治疗各种疾病和状况的用途，包括预防或治疗(i)血液病(ii)肾脏疾病、肾病或肾脏疾病并发症；(iii)炎症相关疾病；和/或(iv)氧化应激相关紊乱。
• [EN] SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF OSTEOPOROSIS<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET COMPOSITIONS PHARMACEUTIQUES POUR LA PRÉVENTION ET LE TRAITEMENT DE L'OSTÉOPOROSE
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2016054728A1

  公开（公告）日：2016-04-14

  The present invention concerns the use of compounds for preventing and/or treating osteoporosis, for stimulating bone formation, for stimulating bone remodeling, for stimulating the differentiation and mineralization of osteoblasts, for inhibiting bone resorption and for modulating serum level of adiponectin in a subject. These uses have been found for compounds represented by Formula I and pharmaceutically acceptable salts thereof. wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F or OH; R2 is H, F, OH, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH or CH2Ph; R4 is H, F, or OH; Q is 1) (CH2)mC(O)OH wherein m is 1 or 2, 2) CH(F)-C(O)OH, 3) CF2-C(O)OH or 4) C(O)-C(O)OH.

  本发明涉及用于预防或治疗骨质疏松症、刺激骨骼形成、刺激骨骼重塑、刺激成骨细胞的分化和矿化、抑制骨吸收以及调节受试者血清中脂联素水平的化合物的用途。已经发现，这些用途适用于由公式I表示的化合物及其药用可接受的盐。其中A是C5烷基、C6烷基、C5烯基、C6烯基、C(O)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n是3或4；R1是H、F或OH；R2是H、F、OH、C6烷基、C5烯基、C6烯基、C(O)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n是3或4；R3是H、F、OH或CH2Ph；R4是H、F或OH；Q是1) (CH2)mC(O)OH，其中m是1或2，2) CH(F)-C(O)OH，3) CF2-C(O)OH或4) C(O)-C(O)OH。
• [EN] SUBSTITUTED AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR TISSUE SELF-REPAIR AND REGENERATION<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS ET COMPOSITIONS PHARMACEUTIQUES POUR AUTO-RÉPARATION ET RÉGÉNÉRATION DE TISSU
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2016074068A1

  公开（公告）日：2016-05-19

  Described herein are compounds of Formula I, or pharmaceutically acceptable salts thereof, or combinations thereof, as well as uses thereof. Such uses include promoting tissue self-repair or tissue regeneration of an organ, stimulating the generation of tissue growth, modulating (e.g. increasing) the level of a tissue-repair marker, treating physical injury in an organ, tissue, or cell, promoting wound healing as well as anti-aging applications. Corresponding compositions, methods and uses are also described. Formula I wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, F of OH; R2 is H, F, OH, C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(0)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R3 is H, F, OH, or CH2Ph; R4 is H, F or OH; Q is 1) (CH2),C(0)OH wherein m is 1 or 2 2) CH(CH3)C(0)OH, 3) C(CH3)2C(0)OH, 4) CH(F)-C(0)OH, 5) CF2-C(0)OH or 6) C(0)-C(0)OH.

  以下是公式I的化合物，或其药用可接受的盐，或它们的组合，以及它们的用途。这些用途包括促进器官的组织自我修复或组织再生，刺激组织生长的生成，调节（例如增加）组织修复标志物的水平，治疗器官、组织或细胞的物理损伤，促进伤口愈合以及抗衰老应用。还描述了相应的组合物、方法和用途。公式I中，A是C5烷基，C6烷基，C5烯基，C6烯基，C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R1是H，F或OH；R2是H，F，OH，C5烷基，C6烷基，C5烯基，C6烯基，C(0)-(CH2)n-CH3或CH(OH)-(CH2)n-CH3，其中n为3或4；R3是H，F，OH或CH2Ph；R4是H，F或OH；Q是1）（CH2）mC(0)OH，其中m为1或2 2）CH(CH3)C(0)OH，3）C(CH3)2C(0)OH，4）CH(F)-C(0)OH，5）CF2-C(0)OH或6）C(0)-C(0)OH。
• [EN] COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR LE TRAITEMENT DU CANCER
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2012097427A1

  公开（公告）日：2012-07-26

  New uses for phenylketone carboxylate compounds and substituted aromatic compounds of Formula I, Formula I.1, Formula I.2, Formula IA, Formula IB, Formula IC and Formula II and their pharmaceutical acceptable salts for the treatment of cancer. The use of a combination of two of these compounds is described and the use of the combination of one of these compounds with an anticancer agent such as decarbazine, doxorubicin, daunorubicin, cyclophosphamide, busulfex, busulfan, vinblastine, vincristine, bleomycin, etoposide, topotecan, irinotecan, taxotere, taxol, 5-fluorouracil, methotrexate, gemcitabine, cisplatin, carboplatin and chlorambucil.

  苯基酮羧酸酯化合物及取代的芳香族化合物I、I.1、I.2、IA、IB、IC和II及其药学上可接受的盐的新用途，用于治疗癌症。描述了两种这些化合物的组合使用，以及这些化合物中的一种与抗癌剂（如脱碳酰胺、阿霉素、柔红霉素、环磷酰胺、白消安、白消安、长春碱、长春新碱、博来霉素、依托泊苷、拓扑替康、伊立替康、紫杉醇、紫杉醇、5-氟尿嘧啶、甲氨蝶呤、吉西他滨、顺铂、卡铂和苯丁酸氮芥）组合使用的方法。
• [EN] SUBSTITUTED AROMATIC COMPOUNDS FOR THE TREATMENT OF PULMONARY FIBROSIS, LIVER FIBROSIS, SKIN FIBROSIS AND CARDIAC FIBROSIS<br/>[FR] COMPOSÉS AROMATIQUES SUBSTITUÉS POUR TRAITEMENT DE LA FIBROSE PULMONAIRE, DE LA FIBROSE HÉPATIQUE, DE LA FIBROSE CUTANÉE ET DE FIBROSE CARDIAQUE
  申请人：PROMETIC BIOSCIENCES INC

  公开号：WO2014138907A1

  公开（公告）日：2014-09-18

  The present invention relates to substituted aromatic compounds for use in prevention or treatment of various fibrotic diseases and conditions in subjects, including pulmonary fibrosis, liver fibrosis, skin fibrosis and cardiac fibrosis, where the compound has the following formula: or a pharmaceutically acceptable salt thereof, wherein A is C5 alkyl, C6 alkyl, C5 alkenyl, C6 alkenyl, C(O)-(CH2)n-CH3 or CH(OH)-(CH2)n-CH3 wherein n is 3 or 4; R1 is H, OH or F; R2 is H, OH, F or CH2-OH; R3 is H, OH, F or CH2Ph; R4 is H, OH or F; Q is 1 ) (CH2)mC(O)OH wherein m is 1 or 2, 2) CH(CH3)C(O)OH, 3) C(CH3)2C(O)OH, 4) CH(F)-C(O)OH, 5) CF2-C(O)OH, or 6) C(O)-C(O)OH.

  本发明涉及用于预防或治疗主体中的各种纤维化疾病和状况，包括肺纤维化、肝纤维化、皮肤纤维化和心脏纤维化的取代芳香族化合物，其中化合物具有以下公式：或其药学上可接受的盐，其中A为C5烷基，C6烷基，C5烯基，C6烯基，C（O）-（CH2）n-CH3或CH（OH）-（CH2）n-CH3，其中n为3或4；R1为H，OH或F；R2为H，OH，F或CH2-OH；R3为H，OH，F或CH2Ph；R4为H，OH或F；Q为1）（CH2）mC（O）OH，其中m为1或2，2）CH（CH3）C（O）OH，3）C（CH3）2C（O）OH，4）CH（F）-C（O）OH，5）CF2-C（O）OH或6）C（O）-C（O）OH。