3-(2,4-二甲基-3,6-二氧代-1-环己-1,4-二烯基)-3-甲基丁酸 | 133544-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 3-(2,4-二甲基-3,6-二氧代-1-环己-1,4-二烯基)-3-甲基丁酸
• 中文别名: 3-(3',6'-二羰基-2',4'-二甲基环己-1',4'-二烯)-3,3-二甲基丙酸
• 英文名称: 3-(3',6'-dioxo-2',4'-dimethylcyclohexa-1',4'-dienyl)-3,3-dimethylpropionic acid
• 英文别名: 3-(2,4-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-3-methylbutanoic acid
• CAS: 133544-77-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: JHOMCQALRKZDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,4-二甲基-3,6-二氧代-1-环己-1,4-二烯基)-3-甲基丁酸 在 N-甲基吗啉 、 sodium dithionite 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 6-hydroxy-4,4,5,7-tetramethylbenzopyran-2-one
  参考文献：
  名称：

  Development of a Novel Redox-Sensitive Protecting Group for Amines Which Utilizes a Facilitated Lactonization Reaction

  摘要：

  Selective protection and deprotection of functional groups are essential components of modern organic and peptide synthesis. To cope with the demand for the synthesis of organic molecules and peptides with increasing complexity, there has been a need to develop novel protecting groups which are readily cleavable under fundamentally different conditions to ensure selective modifications of specified functional groups. This report is focused on the development of a redox-sensitive amine protecting group using a substituted quinone propionic acid (1a). The key feature of this protecting group is that upon reduction of the quinone 1 to the hydroquinone 2, it undergoes a spontaneous lactonization to release the functional group attached to the carboxyl group (HXR). High yields were achieved for both the protection and deprotection reactions, and the reduction conditions required for the deprotection are very mild (Na2S2O4 or electrochemically) and thus very compatible with most functional groups encountered in organic molecules and peptides.

  DOI：

  10.1021/jo00108a013
• 作为产物：
  描述：

  2,6-二甲基-2,5-环己二烯-1,4-二酮 在 N-溴代丁二酰亚胺(NBS) 、 sodium dithionite 、 甲烷磺酸 、 水 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 4.5h， 生成 3-(2,4-二甲基-3,6-二氧代-1-环己-1,4-二烯基)-3-甲基丁酸
  参考文献：
  名称：

  [EN] TARGETED DELIVERY OF 1, 2, 4, 5-TETRAOXANE COMPOUNDS AND THEIR USES
  [FR] ADMINISTRATION CIBLÉE DE COMPOSÉS DE 1,2,4,5-TÉTRAOXANE ET LEURS UTILISATIONS

  摘要：

  1, 2, 4, 5-tetraoxane compounds and derivatives thereof that have anticancer properties are disclosed. Pharmaceutical compositions and pharmaceutical formulations in unit dosage form suitable for the delivery of the compounds to a subject in need thereof are disclosed. The pharmaceutical compositions or formulations may include one or more active agents in addition to the compounds, such as one or more additional anticancer agents. Methods for treating a cancer, reducing a cancer, or treating or ameliorating one or more symptoms associated with a cancer in a subject are also disclosed. The methods include (i) administering to a subject in need thereof an effective amount of the compound (s). The compound (s) can be administered by oral administration, parenteral administration, inhalation, mucosal administration, or a combination thereof. The compound can selectively kill cancer cells and/or cancer stem cells over non-cancerous cells by triggering ferroptosis in the cancer cells and/or cancer stem cells.

  公开号：

  WO2022161490A1

文献信息

• NQO1激活型6-重氮基-5-氧代-L-正亮氨酸前药及其制备方法和应用
  申请人：中国药科大学

  公开号：CN113461563B

  公开（公告）日：2022-05-10

  本发明公开了一种NQO1激活型6‑重氮基‑5‑氧代‑L‑正亮氨酸前药及其制备方法和应用。由于多数肿瘤细胞中均高表达NQO1，引入NQO1激活的醌酸基团可以实现对肿瘤靶向作用，能够在肿瘤细胞中高效、快速释放DON前药，达到抑制肿瘤增殖的目的。该前药对NQO1显示出高度的亲和性，可以在NQO1高度表达的肿瘤细胞中快速、高效的定向释放出谷氨酰胺代谢拮抗剂DON，进而降低该药物的毒副作用并提高对肿瘤治疗的靶向效率，为抗肿瘤药物的开发提供了新思路。
• Anti-tumuor agents
  申请人：AstraZeneca AB

  公开号：US06346633B1

  公开（公告）日：2002-02-12

  The invention concerns anti-tumour agents of formula (I) wherein each of R1, R2 and R3 has the meanings defined in the specification including hydrogen, (1-4C)alkyl, (3-4)alkenyl, (3-4C)alkynyl, amino, (1-4C)alkylamino and (1-4C)alkoxy; each of R4 and R5 is (1-4C)alkyl; each of R6 and R7 is hydrogen or (1-4C)alkyl; X is oxygen; m is 1 or 2 and each R8 is as defined in the specification; each of Y1 and Y2 is halogeno, (1-4C)alkanesulphonyloxy, benzenesulphonyloxy or phenyl-(1-4C)akanesulphonyloxy; or a pharmaceutically-acceptable salt thereof; provided that at least one of R1, R2 and R3 is other than hydrogen; a process for preparation, pharmaceutical compositions containing them and their use in the production of an anti-proliferative effect.

  该发明涉及式(I)的抗肿瘤剂，其中R1、R2和R3中的每一个具有规范中定义的含义，包括氢、(1-4C)烷基、(3-4)烯基、(3-4C)炔基、氨基、(1-4C)烷基氨基和(1-4C)烷氧基；R4和R5中的每一个是(1-4C)烷基；R6和R7中的每一个是氢或(1-4C)烷基；X是氧；m为1或2，每个R8如规范中定义；Y1和Y2中的每一个是卤素、(1-4C)烷磺酰氧基、苯磺酰氧基或苯基-(1-4C)烷磺酰氧基；或其药用可接受盐；前提是R1、R2和R3中至少有一个不是氢；一种制备方法，含有它们的药物组合物以及它们在抗增殖作用中的应用。
• SPERMINE PRO-DRUGS
  申请人：UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US20210000769A1

  公开（公告）日：2021-01-07

  Disclosed herein are novel spermine prodrugs and methods of use for treating subjects exhibiting symptoms of a low spermine disorder. Also disclosed are methods of synthesizing spermine prodrugs. Compositions containing spermine prodrugs are also disclosed.

  本文披露了新型的精胺前药及其治疗表现出低精胺症状的受试者的方法。还披露了合成精胺前药的方法。还披露了含有精胺前药的组合物。
• Facilitated Intramolecular Conjugate Addition of Amides of 3-(3‘,6‘-Dioxo-2‘,4‘-dimethyl-1‘,4‘-cyclohexadienyl)-3,3-dimethylpropionic Acid. 2. Kinetics of Degradation
  作者：Michalis G. Nicolaou、Janet L. Wolfe、Richard L. Schowen、Ronald T. Borchardt

  DOI：10.1021/jo961069l

  日期：1996.1.1

  the intramolecular 1,2- or 1,4- conjugate addition of the amide nitrogen to the quinone ring. This conjugate addition was found to be specific base-catalyzed and independent of the para substituent on the aromatic ring of the amine. The predominant route of degradation yielded a five-membered ring spirolactam. By altering the nature of the amine component of the amide, these degradation reactions were

  3-（3'，6'-dioxo-2'，4'-二甲基-1'，4'-环己二烯基）-3,3-二甲基丙酸（Qa）[Qop（aj）]的酰胺的化学稳定性研究为了确定该氧化还原敏感系统作为有机合成中潜在的前药促发基团或氧化还原敏感保护基的实用性，进行了研究。这项研究表明，苯胺衍生物[Qop（ad）]的醌丙酰胺在中等酸性条件下（pH 4.5-6.0）经历了快速降解，从而产生了分子内1,2-或1,4-共轭物添加的降解产物。酰胺氮连接至醌环。发现该共轭加成是特定的碱催化的并且独立于胺的芳环上的对取代基。降解的主要途径产生了五元环螺内酰胺。通过改变酰胺的​​胺成分的性质，防止了这些降解反应。发现Qa的酰胺比苯胺型[Qop（ej）]的酰胺更稳定，因此被提议作为该潜在的对氧化还原敏感的前药系统和对胺和醇的氧化还原敏感保护基的更合适的候选物。在有机合成中。
• Spermine pro-drugs
  申请人：UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.

  公开号：US11529322B2

  公开（公告）日：2022-12-20

  Disclosed herein are novel spermine prodrugs and methods of use for treating subjects exhibiting symptoms of a low spermine disorder. Also disclosed are methods of synthesizing spermine prodrugs. Compositions containing spermine prodrugs are also disclosed.

  本文公开了新型精胺原药和用于治疗表现出低精胺紊乱症状的受试者的方法。还公开了精氨酸原药的合成方法。还公开了含有精胺原药的组合物。