ethyl 2-methyl-5-hydroxymethylfuran-3-carboxylate | 15341-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 2-methyl-5-hydroxymethylfuran-3-carboxylate
• 英文别名: ethyl 5-hydroxymethyl-2-methylfuran-3-carboxylate；3-ethoxycarbonyl-5-hydroxymethyl-2-methylfuran；ethyl hydroxymethylfuroate；5-hydroxymethyl-2-methyl-furan-3-carboxylic acid ethyl ester；5-Hydroxymethyl-2-methyl-furan-3-carbonsaeure-aethylester；5-Methyl-2-hydroxymethyl-4-ethoxycarbonyl-furan；3-Furancarboxylic acid, 5-(hydroxymethyl)-2-methyl-, ethyl ester；ethyl 5-(hydroxymethyl)-2-methylfuran-3-carboxylate
• CAS: 15341-70-5
• 化学式: C₉H₁₂O₄
• mdl: MFCD30479344
• 分子量: 184.192
• InChiKey: SPXOPKHVDHJGLM-UHFFFAOYSA-N

物化性质

• 沸点：
  117 °C(Press: 0.2 Torr)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-hydroxymethylfuran-3-carboxylate 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 乙基5-甲酰基-2-甲基呋喃-3-羧酸酯
  参考文献：
  名称：

  Pevzner; Ignat'ev; Ionin, Russian Journal of General Chemistry, 1997, vol. 67, # 11, p. 1710 - 1718

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基5-甲酰基-2-甲基呋喃-3-羧酸酯 在 sodium tetrahydroborate 作用下， 反应 0.5h， 生成 ethyl 2-methyl-5-hydroxymethylfuran-3-carboxylate
  参考文献：
  名称：

  通过原位筛选（pyrrolidin-2-yl）triazoles库快速发现有效的α-岩藻糖苷酶抑制剂。

  摘要：

  通过铜催化的炔基亚氨基环戊醇与一组市售和合成的叠氮化物的铜催化合成（吡咯烷-2-基）三唑的小文库。对所得三唑对α-岩藻糖苷酶活性的原位筛选已鉴定出该酶最有效和选择性最强的吡咯烷衍生抑制剂之一（Ki = 4 nM）。

  DOI：

  10.1039/c4ob00931b

文献信息

• Chemical, photochemical and enzymatic approach to furylhydroperoxides
  作者：Arrigo Scettri、Francesco Bonadies、Alessandra Lattanzi、Laura Palombi、Silvia Pesci

  DOI：10.1016/s0040-4020(97)10135-1

  日期：1997.12

  Furylhydroperoxides are accessible by three different methodologies. In the enzymatic approach, lypoxygenase is employed on non lipid-like substrates. Transition metal catalyzed epoxidation of allylic alcohols is strongly dependent on the structure of the involved hydroperoxide.

  呋喃基氢过氧化物可通过三种不同的方法获得。在酶促方法中，在非脂质样底物上使用了加氧合酶。过渡金属催化的烯丙基醇的环氧化强烈依赖于所涉及的氢过氧化物的结构。
• [EN] PIPERIDINE DERIVATIVES FOR USE IN THE TREATMENT OF PANCREATIC CANCER<br/>[FR] DÉRIVÉS DE PIPÉRIDINE UTILISABLES DANS LE TRAITEMENT DU CANCER DU PANCRÉAS
  申请人：CENTRE HOSPITALIER UNIV VAUDOIS CHUV

  公开号：WO2018024907A1

  公开（公告）日：2018-02-08

  The present invention relates to novel piperidine derivatives having better cell growth inhibitory activities toward cancer cell cultures and, more particularly, PANC-1 cancer cell cultures than FK866. Accordingly, the present invention relates to compounds of formula (I), wherein Ar1 is aryl or heteroaryl, which are optionally substituted by one, two or three substituents selected from lower alkyl; lower alkoxy; formyl; hydroxyl; lower alkyl substituted by lower alkoxy or hydroxyl; A is CnH2n, CnH2n-2 or CnH2n-4, wherein n=4,5,6,7; B is =N-CN, oxo (=0), thio (=S); D is NH, -CH=CH-; Ar2 is aryl or heteroaryl which are optionally substituted by one, two or three halogen substituents; wherein, if B is oxo (=0), Ar1 and Ar2 are not simultaneously phenyl and pyridine-3-yl; B and D are not simultaneously =N-CN and -CH=CH-, or a pharmaceutically acceptable salt, a racemic mixture or its corresponding enantiomers and/or optical isomers. The compounds of formula (I) and their pharmaceutically usable addition salts possess valuable pharmacological properties. Specifically, it has been found that the compounds of the present invention, alone or in combination with other therapeutic active compounds, have an activity as chemotherapeutic agents against cancer and, more particularly, pancreatic cancers.

  本发明涉及具有更好的细胞生长抑制活性的新型哌啶衍生物，特别是对PANC-1癌细胞培养物比FK866具有更好的抑制活性。因此，本发明涉及式（I）的化合物，其中Ar1为芳基或杂环芳基，可以选择地由一个、两个或三个从低碳烷基、低碳氧基、甲酰基、羟基、被低碳氧基或羟基取代的低碳烷基所取代；A为CnH2n、CnH2n-2或CnH2n-4，其中n=4,5,6,7；B为=N-CN、氧（=O）、硫（=S）；D为NH、-CH=CH-；Ar2为芳基或杂环芳基，可以选择地由一个、两个或三个卤素取代；其中，如果B为氧（=O），Ar1和Ar2不同时为苯基和吡啶-3-基；B和D不同时为=N-CN和-CH=CH-，或其药学上可接受的盐、拉氏混合物或其对应的对映体和/或光学异构体。式（I）的化合物及其药学可用的加盐具有有价值的药理学性质。具体而言，已发现本发明的化合物，单独或与其他治疗活性化合物结合，具有作为化疗药物的活性，特别是对抗癌症和更特别是胰腺癌的活性。
• PIPERIDINE DERIVATIVES FOR USE IN THE TREATMENT OF PANCREATIC CANCER
  申请人：Centre Hospitalier Universitaire Vaudois (CHUV)

  公开号：EP3279192A1

  公开（公告）日：2018-02-07

  The present invention relates to novel piperidine derivatives having better cell growth inhibitory activities toward PANC-1 cancer cell cultures than FK866. Accordingly, the present invention relates to compounds of formula I, wherein Ar1 is aryl or heteroaryl, which are optionally substituted by one, two or three substituents selected from lower alkyl; lower alkoxy; formyl; hydroxyl; lower alkyl substituted by lower alkoxy or hydroxyl; A is CnH2n, CnH2n-2 or CnH2n-4, wherein n=4,5,6,7; B is =N-CN, oxo (=O), thio (=S); D is NH, -CH=CH-; Ar2 is aryl or heteroaryl which are optionally substituted by one, two or three halogen substituents; wherein, if B is oxo (=O), Ar1 and Ar2 are not simultaneously phenyl and pyridine-3-yl; B and D are not simultaneously =N-CN and -CH=CH-, or a pharmaceutically acceptable salt, a racemic mixture or its corresponding enantiomers and/or optical isomers. The compounds of formula I and their pharmaceutically usable addition salts possess valuable pharmacological properties. Specifically, it has been found that the compounds of the present invention, alone or in combination with other therapeutic active compounds, have an activity as chemotherapeutic agents against pancreatic cancers.

  本发明涉及新型哌啶衍生物，其对 PANC-1 癌细胞培养物的细胞生长抑制活性优于 FK866。因此，本发明涉及式 I 的化合物，其中 Ar1 是芳基或杂芳基，可任选被一个、两个或三个取代基取代，这些取代基选自低级烷基；低级烷氧基；甲酰基；羟基；被低级烷氧基或羟基取代的低级烷基；A 是 CnH2n、CnH2n-2 或 CnH2n-4，其中 n=4、5、6、7；B 是 =N-CN、氧代（=O）、硫代（=S）；D是NH、-CH=CH-；Ar2是芳基或杂芳基，可任选被一个、两个或三个卤素取代基取代；其中，如果B是氧代（=O），Ar1和Ar2不同时是苯基和吡啶-3-基；B和D不同时是=N-CN和-CH=CH-，或药学上可接受的盐、外消旋混合物或其相应的对映体和/或光学异构体。式 I 化合物及其药用加成盐具有宝贵的药理特性。具体地说，已经发现本发明的化合物，单独或与其他治疗活性化合物结合，具有作为化疗剂对抗胰腺癌的活性。
• Piperidine derivatives for use in the treatment of pancreatic cancer
  申请人：CENTRE HOSPITALIER UNIVERSITAIRE VAUDOIS CHUV

  公开号：US10894785B2

  公开（公告）日：2021-01-19

  The present invention relates to novel piperidine derivatives having better cell growth inhibitory activities toward cancer cell cultures and, more particularly, PANC-1 cancer cell cultures than FK866. Accordingly, the present invention relates to compounds of formula I, wherein Ar1 is aryl or heteroaryl, which are optionally substituted by one, two or three substituents selected from lower alkyl; lower alkoxy; formyl; hydroxyl; lower alkyl substituted by lower alkoxy or hydroxyl; A is CnH2n, CnH2n-2 or CnH2n-4, wherein n=4,5,6,7; B is ═N—CN, oxo (═O), thio (═S); D is NH, —CH═CH—; Ar2 is aryl or heteroaryl which are optionally substituted by one, two or three halogen substituents; wherein, if B is oxo (═O), Ar1 and Ar2 are not simultaneously phenyl and pyridine-3-yl; B and D are not simultaneously ═N—CN and —CH═CH—, or a pharmaceutically acceptable salt, a racemic mixture or its corresponding enantiomers and/or optical isomers. The compounds of formula I and their pharmaceutically usable addition salts possess valuable pharmacological properties. Specifically, it has been found that the compounds of the present invention, alone or in combination with other therapeutic active compounds, have an activity as chemotherapeutic agents against cancer and, more particularly, pancreatic cancers.

  本发明涉及新型哌啶衍生物，该衍生物对癌细胞培养物，尤其是 PANC-1 癌细胞培养物具有比 FK866 更好的细胞生长抑制活性。因此，本发明涉及式 I 的化合物，其中 Ar1 是芳基或杂芳基，可任选被一个、两个或三个取代基取代，这些取代基选自低级烷基；低级烷氧基；甲酰基；羟基；被低级烷氧基或羟基取代的低级烷基；A 是 CnH2n、CnH2n-2 或 CnH2n-4，其中 n=4、5、6、7；B 是═N-CN、氧代（═O）、硫代（═S）；D是NH、-CH═CH-；Ar2是芳基或杂芳基，可任选被一个、两个或三个卤素取代基取代；其中，如果B是氧代（═O），Ar1和Ar2不能同时是苯基和吡啶-3-基；B和D不能同时是═N-CN和-CH═CH-，或药学上可接受的盐、外消旋混合物或其相应的对映体和/或光学异构体。式 I 化合物及其药用加成盐具有宝贵的药理特性。具体地说，已经发现本发明的化合物，单独或与其它治疗活性化合物结合使用，具有作为化疗剂对抗癌症，特别是胰腺癌的活性。
• Lopez Aparicio et al., Anales de la Real Sociedad Espanola de Fisica y Quimica, 1958, vol. <B> 54, p. 705,712
  作者：Lopez Aparicio et al.

  DOI：——

  日期：——