3-(3,4-dichlorophenyl)-spiro (oxirane-2,2'-indan)-1',3'-dione | 439125-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3-(3,4-dichlorophenyl)-spiro (oxirane-2,2'-indan)-1',3'-dione
• 英文别名: 3-(3,4-Dichlorophenyl)-spiro (oxirane-2, 2'-indan)-1',3'-dione；3'-(3,4-dichlorophenyl)spiro[indene-2,2'-oxirane]-1,3-dione
• CAS: 439125-83-4
• 化学式: C₁₆H₈Cl₂O₃
• 分子量: 319.144
• InChiKey: JVGWBQQHBUSBGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(3,4-dichlorophenyl)-spiro (oxirane-2,2'-indan)-1',3'-dione 在 sodium hydroxide 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 生成 sodium;(3'R,4'S,5'R)-4'-[(2-acetamidophenyl)carbamoyl]-5'-(3,4-dichlorophenyl)-1,3-dioxospiro[indene-2,2'-oxolane]-3'-carboxylate
  参考文献：
  名称：

  Optimization and determination of the absolute configuration of a series of potent inhibitors of human papillomavirus type-11 E1–E2 protein–protein interaction: A combined medicinal chemistry, NMR and computational chemistry approach

  摘要：

  We have previously reported the discovery and initial SAR optimization of the first series of inhibitors of the human papillomavirus type-11 (HPV11) E1-E2 protein-protein interaction. These inhibitors featured an indandione system spiro-fused onto an all syn substituted tetrahydrofuran ring. In this paper, we report new SAR efforts which have led to the identification of the first low nanomolar inhibitor of the HPV11 E1-E2 protein-protein interaction. In addition, we report a combined NMR and computational chemistry approach which allowed the successful determination of the absolute stereochernistry of the active species originating from the initial racemic lead. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.036
• 作为产物：
  描述：

  2-(3,4-dichloro-benzylidene)-indane-1,3-dione 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 3-(3,4-dichlorophenyl)-spiro (oxirane-2,2'-indan)-1',3'-dione
  参考文献：
  名称：

  人乳头瘤病毒11型E1E2蛋白蛋白质相互作用的第一个抑制剂的结构阐明。

  摘要：

  鉴定了一系列新型的HPV11 E1E2蛋白相互作用抑制剂。这些抑制剂是通过高通量筛选发现的，其特征在于将茚满二酮系统螺合到适当取代的四氢呋喃环上。令人惊讶的是，早期的稳定性研究表明，在结合测定缓冲液中，该特定系列的化合物易于转化为相应的羧酸盐。NMR和质谱技术用于阐明这些产品的结构及其产生机理。

  DOI：

  10.1002/hlca.200390287

文献信息

• Inhibitors of papilloma virus
  申请人：——

  公开号：US20030064985A1

  公开（公告）日：2003-04-03

  A compound of formula (I) or its enantiomers or diastereoisomers thereof: 1 wherein: A,; X, W, R 1 , Y; R 3 ; and R 4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.

  一种具有化学式（I）或其对映体或非对映异构体的化合物： 其中：A，X，W，R1，Y，R3和R4如本文所定义。 该发明的化合物可用作乳头瘤病毒E1-E2-DNA复合物的抑制剂。该发明还提供了一种治疗或预防人类乳头瘤病毒感染的方法。
• Structure Elucidation of the First Inhibitors of Human Papillomavirus Type 11 E1E2 ProteinProtein Interaction
  作者：Christiane Yoakim、Nathalie Goudreau、Graham A. McGibbon、Jeff O'Meara、Peter W. White、William W. Ogilvie

  DOI：10.1002/hlca.200390287

  日期：2003.10

  A novel series of inhibitors of the HPV11 E1E2 proteinprotein interaction was identified. These inhibitors, which were discovered as a result of high-throughput screening, feature an indandione system spiro-fused onto an appropriately substituted tetrahydrofuran ring. Early stability studies indicated, surprisingly, that this particular series of compounds were readily converted, in binding assay buffer

  鉴定了一系列新型的HPV11 E1E2蛋白相互作用抑制剂。这些抑制剂是通过高通量筛选发现的，其特征在于将茚满二酮系统螺合到适当取代的四氢呋喃环上。令人惊讶的是，早期的稳定性研究表明，在结合测定缓冲液中，该特定系列的化合物易于转化为相应的羧酸盐。NMR和质谱技术用于阐明这些产品的结构及其产生机理。
• Inhibitors of Papilloma Virus
  申请人：Yoakim Christiane

  公开号：US20060235010A1

  公开（公告）日：2006-10-19

  A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A, X, W, R 1 , Y; R 3 ; and R 4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.

  公式（I）或其对映体或非对映异构体的化合物：其中：A、X、W、R1、Y；R3；和R4如定义所述。本发明的化合物可用作乳头瘤病毒E1-E2-DNA复合物的抑制剂。本发明还提供了一种治疗或预防人乳头瘤病毒感染的方法。
• INHIBITORS OF PAPILLOMA VIRUS
  申请人：Yoakim Christiane

  公开号：US20100041649A1

  公开（公告）日：2010-02-18

  A compound of formula (I) or its enantiomers or diastereoisomers thereof: wherein: A, X, W, R 1 , Y; R 3 ; and R 4 are as defined herein. The compounds of the invention may be used as inhibitors of the papilloma virus E1-E2-DNA complex. The invention further provides a method of treating or preventing human papilloma virus infection.

  化合物(I)的公式或其对映体或二对映异构体：其中：A、X、W、R1、Y；R3；和R4如本文所定义。本发明的化合物可用作乳头瘤病毒E1-E2-DNA复合物的抑制剂。本发明还提供了一种用于治疗或预防人乳头瘤病毒感染的方法。
• Discovery of the first series of inhibitors of human papillomavirus type 11: inhibition of the assembly of the E1–E2–Origin DNA complex
  作者：Christiane Yoakim、William W. Ogilvie、Nathalie Goudreau、Julie Naud、Bruno Haché、Jeff A. O'Meara、Michael G. Cordingley、Jacques Archambault、Peter W. White

  DOI：10.1016/s0960-894x(03)00510-9

  日期：2003.8

  We have discovered a series of inhibitors of the assembly of the HPV11 E1-E2-origin DNA complex, which incorporate an indandione fused to a substituted tetrahydrofuran. (C) 2003 Elsevier Ltd. All rights reserved.