2-(4-bromo-2-thienyl)-2-ethyl-[1,3]dioxolane | 341555-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-bromo-2-thienyl)-2-ethyl-[1,3]dioxolane
• 英文别名: 2-(4-bromothiophen-2-yl)-2-ethyl-1,3-dioxolane
• CAS: 341555-91-7
• 化学式: C₉H₁₁BrO₂S
• 分子量: 263.155
• InChiKey: LCRQUPOHVDOIKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  313.4±42.0 °C(Predicted)
• 密度：
  1.489±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-bromo-2-thienyl)-2-ethyl-[1,3]dioxolane 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium permanganate 、 copper(l) iodide 、 正丁基锂 、 水 、 碘 、 碳酸氢钠 、 sodium carbonate 、 magnesium sulfate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2-amino-5-[5-(2-ethyl-[1,3]dioxolan-2-yl)-thiophen-3-yl]-3-methyl-5-(3-pyrimidin-5-yl-phenyl)-3,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: Exploring the S2′ region

  摘要：

  The proteolytic enzyme beta-secretase (BACE1) plays a central role in the synthesis of the pathogenic beta-amyloid in Alzheimer's disease. SAR studies of the S2' region of the BACE1 ligand binding pocket with pyrazolyl and thienyl P2' side chains are reported. These analogs exhibit low nanomolar potency for BACE1, and demonstrate >50-to 100-fold selectivity for the structurally related aspartyl proteases BACE2 and cathepsin D. Small groups attached at the nitrogen of the P2' pyrazolyl moiety, together with the P3 pyrimidine nucleus projecting into the S3 region of the binding pocket, are critical components to ligand's potency and selectivity. P2' thiophene side chain analogs are highly potent BACE1 inhibitors with excellent selectivity against cathepsin D, but only modest selectivity against BACE2. The cell-based activity of these new analogs tracked well with their increased molecular binding with EC50 values of 0.07-0.2 mu M in the ELISA assay for the most potent analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.057
• 作为产物：
  描述：

  1-(2-噻吩基)-1-丙酮 在 aluminum (III) chloride 、 溴 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-bromo-2-thienyl)-2-ethyl-[1,3]dioxolane
  参考文献：
  名称：

  New pyrazolyl and thienyl aminohydantoins as potent BACE1 inhibitors: Exploring the S2′ region

  摘要：

  The proteolytic enzyme beta-secretase (BACE1) plays a central role in the synthesis of the pathogenic beta-amyloid in Alzheimer's disease. SAR studies of the S2' region of the BACE1 ligand binding pocket with pyrazolyl and thienyl P2' side chains are reported. These analogs exhibit low nanomolar potency for BACE1, and demonstrate >50-to 100-fold selectivity for the structurally related aspartyl proteases BACE2 and cathepsin D. Small groups attached at the nitrogen of the P2' pyrazolyl moiety, together with the P3 pyrimidine nucleus projecting into the S3 region of the binding pocket, are critical components to ligand's potency and selectivity. P2' thiophene side chain analogs are highly potent BACE1 inhibitors with excellent selectivity against cathepsin D, but only modest selectivity against BACE2. The cell-based activity of these new analogs tracked well with their increased molecular binding with EC50 values of 0.07-0.2 mu M in the ELISA assay for the most potent analogs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.057

文献信息

• Vitamin D analogues
  申请人：Galderma Research & Development, S.N.C.

  公开号：US06706725B1

  公开（公告）日：2004-03-16

  The invention relates to novel bicyclic compounds having the general formula (I): as well as to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, in carcinology and in the field of autoimmune diseases and that of organ or tissue transplants in particular), or alternatively in cosmetic compositions.

  这项发明涉及具有通式（I）的新型双环化合物，以及用于制备它们的方法，以及它们在用于人类或兽医药物组合物中的用途（特别是在皮肤病学、癌症学、自身免疫疾病以及器官或组织移植领域），或者在化妆品组合物中的用途。
• Amino-5-(5-membered)hetero-arylimidazolone compounds and the use thereof for beta-secretase modulation
  申请人：Malamas Sotirios Michael

  公开号：US20070004786A1

  公开（公告）日：2007-01-04

  The present invention provides a 2-amino-5-heteroaryl-5-phenylimidazolone compound of formula I The present invention also provides methods for the use thereof to inhibit β-secretase (BACE) and treat β-amyloid deposits and neurofibrillary tangles

  本发明提供了一种式I的2-氨基-5-杂环基-5-苯基咪唑酮化合物。本发明还提供了利用该化合物抑制β-分泌酶（BACE）并治疗β-淀粉样沉积和神经原纤维缠结的方法。
• AMINO-5-(5-MEMBERED)HETERO-ARYLIMIDAZOLONE COMPOUNDS AND THE USE THEREOF FOR beta-SECRETASE MODULATION
  申请人：Malamas Michael Sotirios

  公开号：US20080306091A1

  公开（公告）日：2008-12-11

  The present invention provides a 2-amino-5-heteroaryl-5-phenylimidazolone compound of formula I The present invention also provides methods for the use thereof to inhibit β-secretase (BACE) and treat β-amyloid deposits and neurofibrillary tangles

  本发明提供了一种式为I的2-氨基-5-杂环基-5-苯基咪唑酮化合物。本发明还提供了使用该化合物的方法，以抑制β-分泌酶（BACE）并治疗β-淀粉样沉积和神经原纤维缠结。
• Amino-5-(5-membered)heteroarylimidazolone Compounds And The Use Thereof For Beta-secretase Modulation
  申请人：Malamas Michael Sotirios

  公开号：US20100168106A1

  公开（公告）日：2010-07-01

  The present invention provides a 2-amino-5-heteroaryl-5-phenylimidazolone compound of formula I The present invention also provides methods for the use thereof to inhibit β-secretase (BACE) and treat β-amyloid deposits and neurofibrillary tangles

  本发明提供了一种式为I的2-氨基-5-杂环基-5-苯基咪唑酮化合物。本发明还提供了使用该化合物的方法，以抑制β-分泌酶（BACE）并治疗β-淀粉样沉积和神经原纤维缠结。
• ANALOGUES DE LA VITAMINE D
  申请人：Galderma Research & Development, S.N.C.

  公开号：EP1235824A1

  公开（公告）日：2002-09-04