(-)-伊洛福芬 | 158440-71-2

• 物质功能分类: 原料药
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (-)-伊洛福芬
• 中文别名: 伊洛福芬
• 英文名称: Irofulven
• 英文别名: (-)-6-hydroxymethylacylfulvene；[14C]-Irofulven；MGI-114；(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
• CAS: 158440-71-2
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: NICJCIQSJJKZAH-AWEZNQCLSA-N

物化性质

• 熔点：
  127-129°
• 比旋光度：
  D25 -639° (c = 0.096 in ethanol)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  -20°C

制备方法与用途

Irofulven（MGI 114）是一种类似于伊卢定S的化合物，也是一种DNA烷基化剂。它能够抑制DNA复制、诱导肿瘤细胞凋亡，并展现出强烈的抗肿瘤活性[1][2]。

反应信息

• 作为反应物：
  描述：

  (-)-伊洛福芬 在 硫酸 、 sodium cyanoborohydride 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 152.0h， 生成 NCS-690179
  参考文献：
  名称：

  Structure−Activity Studies of Antitumor Agent Irofulven (Hydroxymethylacylfulvene) and Analogues

  摘要：

  Many analogues of the antitumor agent irofulven have been readily prepared by replacing the allylic hydroxyl with a variety of nucleophiles. Analogues of acylfulvene (the precursor to irofulven) were also prepared by Michael reaction with acrolein. The toxicity of the analogues was determined, as well as preclinical antitumor activity. Several analogues exhibited good activity in mouse xenografts. Structural requirements for activity are discussed.

  DOI：

  10.1021/jo010458z
• 作为产物：
  描述：

  隐陡头菌素; 隐杯伞素; 月亮霉素 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (-)-伊洛福芬
  参考文献：
  名称：

  Synthesis of [3H]-illudin S, [3H]-acylfulvene, [3H] & [14C]-hydroxymethylacylfulvene (MGI 114)

  摘要：

  Tritiated derivatives of the toxic sesquiterpene illudin S (1) have been prepared by fermentation of Omphalotus illudens in the presence of [H-3]-sodium acetate. [H-3]-illudin S was converted to antitumor [H-3]-acylfulvene (4) by treatment with dilute sulfuric acid. Antitumor [C-14]-hydroxymethylacylfulvene (5) was best prepared by reacting acylfulvene with [C-14]-paraformaldehyde in dilute sulfuric acid.

  DOI：

  10.1002/(sici)1099-1344(199804)41:4<279::aid-jlcr86>3.0.co;2-j

文献信息

• [EN] ASH1L INHIBITORS AND METHODS OF TREATMENT THEREWITH<br/>[FR] INHIBITEURS DE ASH1L ET MÉTHODES DE TRAITEMENT AU MOYEN DE CEUX-CI
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2017197240A1

  公开（公告）日：2017-11-16

  Provided herein are small molecule inhibitors of ASH1L activity and small molecules that facilitate ASH1L degradation and methods of use thereof for the treatment of disease, including acute leukemia, solid cancers and other diseases dependent on activity of ASH1L.

  本文提供了ASH1L活性的小分子抑制剂，促进ASH1L降解的小分子以及它们的使用方法，用于治疗疾病，包括急性白血病、实体肿瘤和其他依赖于ASH1L活性的疾病。
• [EN] ERK INHIBITORS<br/>[FR] INHIBITEURS D'ERK
  申请人：MERCK SHARP & DOHME

  公开号：WO2016100050A1

  公开（公告）日：2016-06-23

  The present invention provides a compound of Formula (I) or the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are ERK2 inhibitors. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and a pharmaceutically acceptable carrier. The invention also provides a pharmaceutical composition comprising an effective amount of at least one compound of Formula (I) and an effective amount of at least one other pharmaceutically active ingredient (such as, for example, a chemotherapeutic agent), and a pharmaceutically acceptable carrier.

  本发明提供了一种化合物(I)或其药学上可接受的盐、酯和前药，这些化合物是ERK2抑制剂。该发明还提供了一种包括至少一种化合物(I)和药学上可接受的载体的有效量的药物组合物。该发明还提供了一种包括至少一种化合物(I)的有效量和至少一种其他药学活性成分的有效量（例如，化疗药物等）以及药学上可接受的载体的药物组合物。
• THERAPEUTIC COMPOUNDS AND COMPOSITIONS
  申请人：Salituro Francesco G.

  公开号：US20120172349A1

  公开（公告）日：2012-07-05

  Compounds and compositions comprising compounds that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  本文描述了包含调节丙酮酸激酶M2（PKM2）的化合物和组合物。本文还描述了利用调节PKM2的化合物治疗癌症的方法。
• [EN] NOVEL N- (4- (AZETIDINE - 1 - CARBONYL) PHENYL) - (HETERO - ) ARYLSULFONAMIDE DERIVATIVES AS PYRUVATE KINASE M2 (PMK2) MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS DE N-(4-(AZÉTIDINE- 1 - CARBONYL) PHÉNYL)-(HÉTÉRO-) ARYLSULFONAMIDE EN TANT QUE MODULATEURS DE LA PYRUVATE KINASE M2 (PMK2)
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2012083246A1

  公开（公告）日：2012-06-21

  Compounds of general Formula (I), and compositions comprising compounds of general formula I that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  通用式(I)化合物和包含调节丙酮酸激酶M2（PKM2）的通用式I化合物的组合物在此处进行描述。此外，还描述了利用调节PKM2的化合物治疗癌症的方法。
• [EN] THERAPEUTIC COMPOUNDS AND COMPOSITIONS<br/>[FR] COMPOSÉS ET COMPOSITIONS THÉRAPEUTIQUES
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2014139325A1

  公开（公告）日：2014-09-18

  Compounds of general formula (I) and compositions comprising compounds of general formula (I) that modulate pyruvate kinase are described herein. Also described herein are methods of using the compounds that modulate pyruvate kinase in the treatment of diseases.

  本文描述了一般式（I）化合物和包含调节丙酮酸激酶的一般式（I）化合物的组合物。本文还描述了利用调节丙酮酸激酶的这些化合物治疗疾病的方法。