methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate | 615581-18-5

• 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: methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate
• 英文别名: 4-[3-[1,3]-Dioxolan-2-yl-propyl)benzoic acid methyl ester
• CAS: 615581-18-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ANBJPDXORCRYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 4-(4-氧代丁基)苯甲酸甲酯
  参考文献：
  名称：

  Structural determinants for histamine H1 affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs

  摘要：

  In the late 1980's reports linking the non-sedating antihistamines terfenadine and astemizole with torsades de pointes, a form of ventricular tachyarrhythmia that can degenerate into ventricular fibrillation and sudden death, appeared in the clinical literature. A substantial body of evidence demonstrates that the arrhythmogenic effect of these cardiotoxic antihistamines, as well as a number of structurally related compounds, results from prolongation of the QT interval due to suppression of specific delayed rectifier ventricular K+ currents via blockade of the hERG-IKr channel. In order to better understand the structural requirements for hERG and H-1 binding for terfenadine, a series of analogs of terfenadine has been prepared and studied in both in vitro and in vivo hERG and H-1 assays. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.047
• 作为产物：
  描述：

  2-(1,3-二氧戊环-2-基)乙基三苯基溴化磷 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 methyl 4-[3-(1,3-dioxolan-2-yl)propyl]benzoate
  参考文献：
  名称：

  Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring

  摘要：

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.

  DOI：

  10.1021/jo034767w

文献信息

• Biologically active acylated amino acid derivatives
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US05620971A1

  公开（公告）日：1997-04-15

  The present invention relates to novel compounds which possess a broad range of useful biological activities. These compounds can maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. They can also suppress, modify, or significantly reduce an immune response, including an autoimmune response in a mammal. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance, for use in multi-drug resistant cancer therapy, and for prevention or treatment of graft rejection and various autoimmune diseases.

  本发明涉及一种新型化合物，其具有广泛的有用生物活性。这些化合物可以维持、增加或恢复细胞对治疗或预防药物的敏感性。它们也可以抑制、改变或显著减少哺乳动物的免疫反应，包括自身免疫反应。本发明还涉及包含这些化合物的制药组合物。本发明的化合物和制药组合物特别适用于治疗多药耐药细胞、预防多药耐药的发展、用于多药耐药癌症治疗，以及预防或治疗移植排斥和各种自身免疫性疾病。
• 1-(2-OXO-ACETYL)-PIPERIDINE-2-CARBOXYLIC ACID DERIVATIVES AS MULTI-DRUG-RESISTENT CANCER CELL SENSITIZERS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP0662958B1

  公开（公告）日：2002-12-11
• US5620971A
  申请人：——

  公开号：US5620971A

  公开（公告）日：1997-04-15
• [EN] 1-(2-OXO-ACETYL)-PIPERIDINE-2-CARBOXYLIC ACID DERIVATIVES AS MULTI-DRUG-RESISTENT CANCER CELL SENSITIZERS<br/>[FR] DERIVES DE L'ACIDE 1-(2-OXO-ACETYL)-PIPERIDINE-2-CARBOXYLIQUE UTILES COMME SENSIBILISATEURS DE CELLULES CANCEREUSES RESISTANT A DE MULTIPLES MEDICAMENTS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：WO1994007858A1

  公开（公告）日：1994-04-14

  (EN) The present invention relates to novel compounds of formula (I) which maintain, increase, or restore sensitivity of cells to therapeutic or prophylactic agents. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well-suited for treatment of multi-drug resistant cells, for prevention of the development of multi-drug resistance and for use in multi-drug resistant cancer therapy.(FR) L'invention concerne de nouveaux composés ayant la formule (I) qui maintiennent, augmentent ou rétablissent la sensibilité de cellules vis-à-vis d'agents thérapeutiques ou prophylactiques. Cette invention concerne également des compositions pharmaceutiques comprenant ces composés. Les composés et les compositions pharmaceutiques de cette invention sont particulièrement appropriés au traitement de cellules qui résistent à de multiples médicaments, à la prévention du développement de la résistance à de multiples médicaments et à leur utilisation en thérapie de cancer résistant à de multiples médicaments.
• Samarium(II)-Promoted Radical Spirocyclization onto an Aromatic Ring
  作者：Hiroaki Ohno、Mitsuaki Okumura、Shin-ichiro Maeda、Hiroki Iwasaki、Ryutaro Wakayama、Tetsuaki Tanaka

  DOI：10.1021/jo034767w

  日期：2003.10.1

  Samarium(II)-mediated spirocyclization onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro[4.5]dec-6-ene-8-carboxylates in moderate to high yields. Utilizing this chemistry, spiro[3.5] and -[5.5] systems, and sterically congested spiro[4.5] systems, were easily synthesized. For the successful conversion, appropriate activation of the aromatic ring has proven to be extremely important: while an ester or amide functionality on the aromatic ring can promote the spirocyclization, a sulfonamide substituent causes ortho cyclization.