4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylic acid 4-isopropenylcyclohex-1-enylmethyl ester | 1361198-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylic acid 4-isopropenylcyclohex-1-enylmethyl ester
• 英文别名: NEO214；1-Pyrrolidinecarboxylic acid, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-, [(4S)-4-(1-methylethenyl)-1-cyclohexen-1-yl]methyl ester；[(4S)-4-prop-1-en-2-ylcyclohexen-1-yl]methyl 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylate
• CAS: 1361198-80-2
• 化学式: C₂₇H₃₅NO₅
• 分子量: 453.579
• InChiKey: JDWAOYHBJSFPSD-PSDZMVHGSA-N

物化性质

• 沸点：
  602.8±55.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

制备方法与用途

NEO214（NEO-214）是一种新型BBB渗透性咯利普兰紫苏醇结合物，对TMZ敏感和TMZ耐药的胶质瘤细胞均显示有效性（T98G IC50=40 μM）。它通过激活ER应激途径引发细胞凋亡，并诱导死亡受体5（DR5）和TNF相关凋亡诱导配体（TRAIL/Apo2L）介导的细胞毒性。该化合物对正常细胞无细胞毒性，在体内小鼠肿瘤模型中减少了神经胶质瘤的进展。

反应信息

• 作为产物：
  描述：

  (S)-(-)-紫苏醇 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.25h， 生成 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidine-1-carboxylic acid 4-isopropenylcyclohex-1-enylmethyl ester
  参考文献：
  名称：

  [EN] TREATMENT OF RECURRENT GIOBLASTOMA WITH PERILLYL ALCOHOL
  [FR] TRAITEMENT DU GLIOBLASTOME RÉCURRENT AVEC DE L'ALCOOL PÉRILLIQUE

  摘要：

  本发明提供了一种利用纯化的柠檬醇鼻内治疗胶质母细胞瘤的方法。使用本发明所披露的方法纯化的柠檬醇治疗复发性胶质母细胞瘤的患者，与历史对照组相比，生存率有所提高。患有异柠檬酸脱氢酶1（IDH1）突变的胶质母细胞瘤患者，与野生型IDH患者相比，生存率有所提高。

  公开号：

  WO2022104041A1

文献信息

• Pharmaceutical Compositions Comprising Deuterium-Enriched Perillyl Alcohol, Iso-Perillyl Alcohol and Derivatives Thereof
  申请人：NEONC TECHNOLOGIES INC.

  公开号：US20160039731A1

  公开（公告）日：2016-02-11

  The present invention, provides for a deuterium-enriched monoterpene or sesquiterpene such as perillyl alcohol, or a deuterium-enriched isomer or analog of monoterpenes or sesquiterpenes, such as isoperillyl alcohol. The present invention also provides for a deuterium-enriched derivative of a monoterpene or sesquiterpene, such as a perillyl alcohol carbamate or a deuterium-enriched derivative of an isomer or analog of a monoterpene or sesquiterpene, such as an isoperillyl alcohol carbamate. The deuterium-enriched derivative may be perillyl alcohol or isoperillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as cancer, comprising the step of delivering to a patient a therapeutically effective amount of a deuterium-enriched compound.

  本发明提供了一种氘增强的单萜或倍半萜，例如桃金娘醇，或者一种氘增强的单萜或倍半萜的同系物或类似物，例如异桃金娘醇。本发明还提供了一种单萜或倍半萜的氘增强衍生物，例如桃金娘醇碳酰胺或一种单萜或倍半萜的同系物或类似物的氘增强衍生物，例如异桃金娘醇碳酰胺。所述氘增强衍生物可以是与治疗剂如化疗剂结合的桃金娘醇或异桃金娘醇。本发明还提供了一种治疗疾病如癌症的方法，包括向患者提供治疗有效量的氘增强化合物。
• [EN] COMPOSITIONS AND METHODS OF DECREASING MEDICATION ERRORS<br/>[FR] COMPOSITIONS ET MÉTHODES DESTINÉES À RÉDUIRE LES ERREURS DE MÉDICATION
  申请人：AZHC LLC

  公开号：WO2019014420A1

  公开（公告）日：2019-01-17

  The present disclosure provides for a method of decreasing medication errors by adding an odorant to a pharmaceutical composition comprising an active agent. The odorant has a distinct and characteristic odor. Thus, the pharmaceutical composition comprising the active agent can be properly identified by the characteristic odor.

  本公开提供了一种通过向包含活性成分的药物组合物中添加香料来减少药物错误的方法。该香料具有独特且特征性的气味。因此，可以通过这种特征性气味正确识别包含活性成分的药物组合物。
• [EN] PHARMACEUTICAL COMPOSITIONS COMPRISING POH DERIVATIVES<br/>[FR] COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES DÉRIVÉS DE POH
  申请人：NEONC TECH INC

  公开号：WO2021061752A1

  公开（公告）日：2021-04-01

  The present invention provides for a derivative of monoterpene or sesquiterpene, such as a perillyl alcohol derivative. For example, the perillyl alcohol derivative may be a perillyl alcohol carbamate. The perillyl alcohol derivative may be perillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as a primary cutaneous lymphoma which may be a cutaneous T cell lymphoma (CTCL). The CTCL may be mycosis fungoides, primary cutaneous anaplastic large cell lymphoma (ALCL), or Sezary syndrome. A patient may be administered a therapeutically effective amount of a derivative of monoterpene (or sesquiterpene).

  本发明提供了一种单萜或倍半萜的衍生物，例如一种胡椒醇衍生物。例如，该胡椒醇衍生物可以是胡椒醇碳酰胺。胡椒醇衍生物可以是胡椒醇与治疗剂如化疗药物结合的产物。本发明还提供了一种治疗疾病的方法，例如原发皮肤淋巴瘤，可能是皮肤T细胞淋巴瘤（CTCL）。CTCL可能是真菌病样皮肤T细胞淋巴瘤、原发皮肤间变性大细胞淋巴瘤（ALCL）或塞扎里综合征。可以向患者施用一种单萜（或倍半萜）衍生物的治疗有效量。
• PHARMACEUTICAL COMPOSITIONS COMPRISING POH DERIVATIVES
  申请人：Neonc Technologies Inc.

  公开号：EP3173080A1

  公开（公告）日：2017-05-31

  The present invention provides for a derivative of monoterpene or sesquiterpene, such as a perillyl alcohol derivative. For example, the perillyl alcohol derivative may be a perillyl alcohol carbamate. The perillyl alcohol derivative may be perillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as cancer, comprising the step of delivering to a patient a therapeutically effective amount of a derivative of monoterpene (or sesquiterpene). The route of administration may vary, and can include, inhalation, intranasal, oral, transdermal, intravenous, subcutaneous or intramuscular injection.

  本发明提供了一种单萜或倍半萜的衍生物，例如紫苏醇衍生物。例如，紫苏醇衍生物可以是紫苏醇氨基甲酸酯。紫苏醇衍生物可以是与化疗剂等治疗剂共轭的紫苏醇。本发明还提供了一种治疗癌症等疾病的方法，包括向患者提供治疗有效量的单萜（或倍半萜）衍生物的步骤。给药途径可以多种多样，包括吸入、鼻内、口服、透皮、静脉注射、皮下注射或肌肉注射。
• Pharmaceutical compositions comprising POH derivatives
  申请人：NeOnc Technologies, Inc.

  公开号：US11013804B2

  公开（公告）日：2021-05-25

  The present invention provides for a perillyl alcohol (POH) carbamate, such as POH-Rolipram. The present invention also provides for a method of treating a disease such as cancer, by delivering to a patient a therapeutically effective amount of POH-Rolipram.

  本发明提供了一种紫苏醇（POH）氨基甲酸酯，如 POH-Rolipram。本发明还提供了一种通过向患者提供治疗有效量的 POH-Rolipram 来治疗癌症等疾病的方法。