(S)-4-((3-bromopropoxy)methyl)-2,2-dimethyl-1,3-dioxolane | 82014-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((3-bromopropoxy)methyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4S)-4-(3-bromopropoxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 82014-46-8
• 化学式: C₉H₁₇BrO₃
• 分子量: 253.136
• InChiKey: NXWLRDBFIOYKNI-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-((3-bromopropoxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.83h， 生成
  参考文献：
  名称：

  Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

  摘要：

  Extracts of the marine sponge Niphates digitalis collected in Dominica showed strong activity in a cell-based assay designed to detect antagonists of the androgen receptor (AR) that could act as lead compounds for the development of a new class of drugs to treat castration recurrent prostate cancer (CRPC). Assay-guided fractionation showed that niphatenones A (3) and B (4), two new glycerol ether lipids, were the active components of the extracts. The structures of 3 and 4 were elucidated by analysis of NMR and MS data and confimed via total synthesis. Biological evaluation of synthetic analogues of the niphatenones has shown that the enantiomers 7 and 8 are more potent than the natural products in the screening assay and defined preliminary SAR for the new AR antagonist pharmacophore, including the finding that the Michael acceptor enone functionality is not required for activity. Niphatenone B (4) and its enantiomer 8 blocked androgen-induced proliferation of LNCaP prostate cancer cells but had no effect on the proliferation of PC3 prostate cancer cells that do not express functional AR, consistent with activity as AR antagonists. Use of the propargyl ether 44 and Click chemistry showed that niphatenone B binds covalently to the activation function-1 (AF1) region of the AR N-terminus domain (NTD).

  DOI：

  10.1021/jm2014056
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 在 四溴化碳 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 (S)-4-((3-bromopropoxy)methyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Niphatenones, Glycerol Ethers from the Sponge Niphates digitalis Block Androgen Receptor Transcriptional Activity in Prostate Cancer Cells: Structure Elucidation, Synthesis, and Biological Activity

  摘要：

  Extracts of the marine sponge Niphates digitalis collected in Dominica showed strong activity in a cell-based assay designed to detect antagonists of the androgen receptor (AR) that could act as lead compounds for the development of a new class of drugs to treat castration recurrent prostate cancer (CRPC). Assay-guided fractionation showed that niphatenones A (3) and B (4), two new glycerol ether lipids, were the active components of the extracts. The structures of 3 and 4 were elucidated by analysis of NMR and MS data and confimed via total synthesis. Biological evaluation of synthetic analogues of the niphatenones has shown that the enantiomers 7 and 8 are more potent than the natural products in the screening assay and defined preliminary SAR for the new AR antagonist pharmacophore, including the finding that the Michael acceptor enone functionality is not required for activity. Niphatenone B (4) and its enantiomer 8 blocked androgen-induced proliferation of LNCaP prostate cancer cells but had no effect on the proliferation of PC3 prostate cancer cells that do not express functional AR, consistent with activity as AR antagonists. Use of the propargyl ether 44 and Click chemistry showed that niphatenone B binds covalently to the activation function-1 (AF1) region of the AR N-terminus domain (NTD).

  DOI：

  10.1021/jm2014056

文献信息

• DIHYDROPYRIDAZINE-3,5-DIONE DERIVATIVE AND PHARMACEUTICALS CONTAINING THE SAME
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20160002251A1

  公开（公告）日：2016-01-07

  The present invention provides a dihydropyridazine-3,5-dione derivative or a salt thereof, or a solvate of the compound or the salt, a pharmaceutical drug, a pharmaceutical composition, a sodium-dependent phosphate transporter inhibitor, and a preventive and/or therapeutic agent for hyperphosphatemia, secondary hyperparathyroidism, chronic renal failure, chronic kidney disease, and arteriosclerosis associated with vascular calcification comprising the compound as an active ingredient, and a method for prevention and/or treatment.

  本发明提供了一种二氢吡啶嗪-3,5-二酮衍生物或其盐，或化合物或盐的溶剂化合物，一种药物，一种药物组合物，一种钠依赖性磷酸盐转运体抑制剂，以及作为活性成分的化合物的高磷血症、继发性甲状旁腺功能亢进症、慢性肾功能衰竭、慢性肾病和与血管钙化相关的动脉硬化的预防和/或治疗剂，以及预防和/或治疗的方法。
• DIHYDROPYRIDAZINE-3,5-DIONE DERIVATIVE
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP2975030A1

  公开（公告）日：2016-01-20

  The present invention provides a dihydropyridazine-3,5-dione derivative or a salt thereof, or a solvate of the compound or the salt, a pharmaceutical drug, a pharmaceutical composition, a sodium-dependent phosphate transporter inhibitor, and a preventive and/or therapeutic agent for hyperphosphatemia, secondary hyperparathyroidism, and chronic renal failure, comprising the compound as an active ingredient, and a method for prevention and/or treatment.

  本发明提供了一种二氢哒嗪-3,5-二酮衍生物或其盐，或该化合物或该盐的溶液剂、一种药物、一种药物组合物、一种钠依赖性磷酸盐转运体抑制剂，以及一种预防和/或治疗高磷血症、继发性甲状旁腺功能亢进症和慢性肾功能衰竭的药物，其中包含该化合物作为活性成分，以及一种预防和/或治疗方法。
• PHARMACEUTICAL CONTAINING SODIUM-DEPENDENT PHOSPHATE TRANSPORTER INHIBITOR AND PHOSPHORUS ADSORBENT FOR USE IN THE PREVENTION, TREATMENT OR SUPPRESSION OF CHRONIC KIDNEY DISEASE, ARTERIOSCLEROSIS ASSOCIATED WITH VASCULAR CALCIFICATION, OR ECTOPIC CALCIFICATION.
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3928779A1

  公开（公告）日：2021-12-29

  The present invention provides a pharmaceutical composition containing, as an active ingredient, a dihydropyridazine-3,5-dione derivative or a salt thereof or a solvate of these, wherein the composition is administered in combination with a phosphorus adsorbent.

  本发明提供了一种药物组合物，其活性成分为二氢哒嗪-3,5-二酮衍生物或其盐或其溶液，其中该组合物与磷吸附剂结合使用。
• PHARMACEUTICAL CONTAINING SODIUM-DEPENDENT PHOSPHATE TRANSPORTER INHIBITOR
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3192511B1

  公开（公告）日：2021-07-14
• EP3757093A1
  申请人：——

  公开号：EP3757093A1

  公开（公告）日：2020-12-30