6-oxo-6H-benzo[c]chromen-3-yl 2-{[(tertbutoxy)carbonyl]amino}acetate | 303016-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-oxo-6H-benzo[c]chromen-3-yl 2-{[(tertbutoxy)carbonyl]amino}acetate
• 英文别名: 3-O-(BOC)-glycinoyldibenzo-α-pyrone；6-oxo-6H-benzo[c]chromen-3-yl N-(tert-butoxycarbonyl)glycinate；(6-oxobenzo[c]chromen-3-yl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 303016-30-0
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: PMZTZHSSGNDWAC-UHFFFAOYSA-N

物化性质

• 沸点：
  564.1±43.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-oxo-6H-benzo[c]chromen-3-yl 2-{[(tertbutoxy)carbonyl]amino}acetate 在 三氟乙酸 、 盐酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到6-oxo-6H-benzo[c]chromen-3-yl 2-aminoacetate hydrochloride
  参考文献：
  名称：

  [EN] PRODRUGS OF UROLITHINS AND USES THEREOF
  [FR] PRODROGUES D'UROLITHINES ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2015097231A9
• 作为产物：
  描述：

  间苯二酚 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 水 为溶剂， 反应 0.34h， 生成 6-oxo-6H-benzo[c]chromen-3-yl 2-{[(tertbutoxy)carbonyl]amino}acetate
  参考文献：
  名称：

  Mitochondria-targeted antioxidants

  摘要：

  本发明涉及一种包含辅酶Q10（CoQ10）、还原辅酶Q10或二苯并α-吡喃氧化物或其氨基酰酯的药用、兽医、营养或个人护理组合物。本发明的组合物能够支持和/或为处于能量代谢功能障碍风险和/或治疗中的个体提供治疗，特别是用于线粒体疾病。

  公开号：

  US20080031862A1

文献信息

• Compositions of stable bioactive metabolites of docosahexaenoic (DHA) and eicosapentaenoic (EPA) acids
  申请人：Ghosal Shibnath

  公开号：US20050282781A1

  公开（公告）日：2005-12-22

  An invention that adduces cogent evidence to establish that oxygenated dibenzo-α-pyrones (DBPs and their conjugates), the major bioactives of shilajit (Ayurvedic vitalizer), have their origin, at least partly, in EPA and DHA. Earlier research has shown that, in mammals, C-20 PUFAs are metabolized by oxygenases and other enzymes to produce short-lived prostaglandins, leukotrienes and thromboxanes that bind to specific G-protein-coupled receptors and signal cellular responses, e.g., inflammation, vasodilation, blood pressure, pain etc. But never before it was suggested/shown that C 20:5n-3 (and C 22:6 n-3 ) PUFAs, e.g., EPA (and DHA), are transformed into stable aromatic metabolites, DBPs, which elicit a large array of bioactivities in the producer organisms and also control the synthesis and metabolism of arachidonate-derived prostaglandins. The major beneficial effects attributed to EPA and DHA are now found to be largely contributed by DBPs and their aminoacyl conjugates and the dibenzo-α-pyrone-chromoproteins (DCPs). Because of the highly unstable nature of EPA and DHA, when administered, they are metabolized into a large array of uncontrolled products, several of which are systemically undesirable. By contrast, DBPs, because of their stability, perform the biological response modifier (BRM) functions in a directed and sustained way. Many of the biological effects of DBPs described in this invention, were earlier attributed to EPA and DHA,—the precursors of DBPs.

  一项发明提供了有力证据，证明含氧二苯并-α-吡喃酮（DBPs及其共轭物）是希拉吉（阿育吠陀活力剂）的主要生物活性成分，其起源至少部分源自EPA和DHA。早期研究表明，在哺乳动物中，C-20多不饱和脂肪酸通过氧化酶和其他酶代谢，产生短寿命的前列腺素、白三烯和血栓素，这些物质结合特定的G蛋白偶联受体并传递细胞反应，如炎症、血管舒张、血压、疼痛等。但以前从未提出/展示过C20:5n-3（和C22:6 n-3）多不饱和脂肪酸，如EPA（和DHA），会转化为稳定的芳香代谢物DBPs，这些物质在生产者生物体中引发大量生物活性，并且还控制花生四烯酸衍生的前列腺素的合成和代谢。现在，归因于EPA和DHA的主要益处效应在很大程度上是由DBPs及其氨酰共轭物和二苯并-α-吡喃酮-色蛋白（DCPs）贡献的。由于EPA和DHA的高度不稳定性，当其被施用时，它们会代谢成大量无法控制的产物，其中一些在全身上是不可取的。相比之下，由于其稳定性，DBPs以有针对性和持续的方式执行生物反应调节剂（BRM）功能。本发明描述的DBPs的许多生物效应，以前被归因于EPA和DHA，即DBPs的前体。
• Prodrugs of urolithins and uses thereof
  申请人：Amazentis SA

  公开号：US11180468B2

  公开（公告）日：2021-11-23

  The invention provides compounds of formula (I) or salts thereof: wherein: A, B, C, D, W, X, Y and Z are as defined in the specification, and at least one of A, B, C, D, W, X, Y and Z is OR1; each R1 being independently H or C(═O)R2, and at least one R1 group being C(═O)R2; where each R2 is selected from: CHR3NHR4, where R4 is H and R3 is a group selected from CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2Ph, CH2-3-(1H-indole), CH2CH2SCH3, CH2OH, CHOHCH3, CH2SH, CH2SeH and CH2PhpOH, wherein said R3 group can optionally be substituted by one or more groups selected from halogen, cyano, nitro, ORA or C1-C4 alkyl; or R3 and R4 together with the C and N atoms to which they are attached form a 5-membered heteroalkyl ring, wherein said heteroalkyl ring can optionally be substituted by one or more groups selected from halogen, cyano, nitro, ORA or C1-C3 alkyl, wherein RA is C1-C4 alkyl optionally substituted with one or more halogen, cyano or nitro groups. The compounds are effective pro-drugs for urolithins and they enable the ready delivery of urolithins to the site in the digestive tract where they can be absorbed into the body.

  本发明提供了式 (I) 化合物或其盐类： 其中 A、B、C、D、W、X、Y 和 Z 如说明书中所定义，且 A、B、C、D、W、X、Y 和 Z 中至少有一个是 OR1；每个 R1 独立地为 H 或 C(═O)R2，且至少有一个 R1 基团为 C(═O)R2；其中每个 R2 选自： CHR3NHR4，其中 R4 为 H，R3 为选自 CH3、CH2CH(CH3)2、CH(CH3)CH2CH3、CH2Ph、CH2-3-(1H-吲哚)、CH2CH2SCH3、CH2OH、CHOHCH3、CH2SH、CH2SeH 和 CH2PhpOH 的基团、 其中所述 R3 基团可任选被一个或多个选自卤素、氰基、硝基、ORA 或 C1-C4 烷基的基团取代； 或 R3 和 R4 与它们所连接的 C 原子和 N 原子一起形成一个 5 元杂烷基环，其中所述杂烷基环可任选被一个或多个选自卤素、氰基、硝基、ORA 或 C1-C3 烷基的基团取代、 其中 RA 是被一个或多个卤素、氰基或硝基任选取代的 C1-C4 烷基。 这些化合物是有效的尿石素原药，可将尿石素直接输送到消化道中可被人体吸收的部位。
• PRODRUGS OF UROLITIHNS AND USES THEREOF
  申请人：Amazentis SA

  公开号：EP3087064B1

  公开（公告）日：2021-09-15
• Prodrugs Of Urolithins And Uses Thereof
  申请人：AMAZENTIS SA

  公开号：US20160332982A1

  公开（公告）日：2016-11-17

  The invention provides compounds of formula (I) or salts thereof: wherein: A, B, C, D, W, X, Y and Z are as defined in the specification, and at least one of A, B, C, D, W, X, Y and Z is OR 1 ; each R 1 being independently H or C(═O)R 2 , and at least one R 1 group being C(═O)R 2 ; where each R 2 is selected from: CHR 3 NHR 4 , where R 4 is H and R 3 is a group selected from CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )CH 2 CH 3 , CH 2 Ph, CH 2 -3-(1H-indole), CH 2 CH 2 SCH 3 , CH 2 OH, CHOHCH 3 , CH 2 SH, CH 2 SeH and CH 2 PhpOH, wherein said R 3 group can optionally be substituted by one or more groups selected from halogen, cyano, nitro, OR A or C 1 -C 4 alkyl; or R 3 and R 4 together with the C and N atoms to which they are attached form a 5-membered heteroalkyl ring, wherein said heteroalkyl ring can optionally be substituted by one or more groups selected from halogen, cyano, nitro, OR A or C 1 -C 3 alkyl, wherein R A is C 1 -C 4 alkyl optionally substituted with one or more halogen, cyano or nitro groups. The compounds are effective pro-drugs for urolithins and they enable the ready delivery of urolithins to the site in the digestive tract where they can be absorbed into the body.
• PRODRUGS OF UROLITHINS AND USES THEREOF
  申请人：Amazentis SA

  公开号：US20190010138A1

  公开（公告）日：2019-01-10

  The invention provides compounds of formula (I) or salts thereof: wherein: A, B, C, D, W, X, Y and Z are as defined in the specification, and at least one of A, B, C, D, W, X, Y and Z is OR 1 ; each R 1 being independently H or C(═O)R 2 , and at least one R 1 group being C(═O)R 2 ; where each R 2 is selected from: CHR 3 NHR 4 , where R 4 is H and R 3 is a group selected from CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )CH 2 CH 3 , CH 2 Ph, CH 2 -3-(1H-indole), CH 2 CH 2 SCH 3 , CH 2 OH, CHOHCH 3 , CH 2 SH, CH 2 SeH and CH 2 PhpOH, wherein said R 3 group can optionally be substituted by one or more groups selected from halogen, cyano, nitro, OR A or C 1 -C 4 alkyl; or R 3 and R 4 together with the C and N atoms to which they are attached form a 5-membered heteroalkyl ring, wherein said heteroalkyl ring can optionally be substituted by one or more groups selected from halogen, cyano, nitro, OR A or C 1 -C 3 alkyl, wherein R A is C 1 -C 4 alkyl optionally substituted with one or more halogen, cyano or nitro groups. The compounds are effective pro-drugs for urolithins and they enable the ready delivery of urolithins to the site in the digestive tract where they can be absorbed into the body.