latifolicinin B | 267228-41-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: latifolicinin B
• 英文别名: (2S)-2-Hydroxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester；ethyl (2S)-2-hydroxy-3-(4-hydroxyphenyl)propanoate
• CAS: 267228-41-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: MPPNCBJETJUYAO-JTQLQIEISA-N

物化性质

• 沸点：
  367.0±27.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  latifolicinin B 、 溴甲苯 、 potassium carbonate 在 silica gel 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 ethyl 3-(4-benzyloxyphenyl)lactate
  参考文献：
  名称：

  Modulators of peroxisome proliferator activated receptors

  摘要：

  公开了一种化合物，其结构式表示为（I）：其中Ar是取代或未取代的芳香族基团。Q是共价键，-CH2-或-CH2CH2-；W是取代或未取代的烷基或取代或未取代的异烷基连接基团，长度为两到十个原子，优选长度为两到七个原子。苯环A可以选择性地用最多四个取代基取代R1和W。R1是-(CH2)n-CH(OR2)-(CH2)mE，-(CH)=C(OR2)-(CH2)mE，-(CH2)n-CH(Y)-(CH2)mE或-(CH)=C(Y)-(CH2)mE；其中E是COOR3，C1-C3-烷基腈，羧酰胺，磺酰胺，酰基磺酰胺或四唑，其中磺酰胺，酰基磺酰胺和四唑可以选择性地用一个或多个取代基取代，独立地选自C1-C6烷基，卤代烷基和芳基-C0-4-烷基；R2是-H，一种脂肪基，一种取代的脂肪基，卤代烷基，一种芳香基，一种取代的芳香基，-COR4，-COOR4，-CONR5R6，-C（S）R4，-C（S）OR4或-C（S）NR5R6；R3是-H，一种脂肪基，一种取代的脂肪基，一种芳香基或一种取代的芳香基；Y是-O-，-CH2-，-CH2CH2-或-CH═CH-，并与苯环A中与R1正交的碳原子键合；R4-R6独立地是-H，一种脂肪基，一种取代的脂肪基，一种芳香基或一种取代的芳香基；n和m独立地为0、1或2。

  公开号：

  US20070276138A1
• 作为产物：
  描述：

  4-羟苯基丙酮酸 在 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.67h， 生成 latifolicinin B
  参考文献：
  名称：

  Latifolicinin A from a Fermented Soymilk Product and the Structure–Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth

  摘要：

  The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of beta-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and L-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their L-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 mu M) and 10-fold less toxic to Detroit-551 normal cells.

  DOI：

  10.1021/acs.jafc.5b04028

文献信息

• Process for the preparation of new antidiabetic agents
  申请人：Dr. Reddy's Laboratories Ltd.

  公开号：US06531596B1

  公开（公告）日：2003-03-11

  The present invention relates to an improved process for the preparation of novel antidiabetic compounds having formula (1) where R1 represents hydrogen or lower alkyl group and X represents hydrogen or halogen atom.

  本发明涉及一种改进的制备新型抗糖尿病化合物的方法，其化学式为（1），其中R1代表氢或较低的烷基基团，X代表氢或卤原子。
• US7192982B2
  申请人：——

  公开号：US7192982B2

  公开（公告）日：2007-03-20
• [EN] NOVEL PHENYLPROPIONIC ACID DERIVATIVES AS PEROXISOME PROLIFERATOR-ACTIVATED GAMMA RECEPTOR MODULATORS, METHOD OF THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAUX DÉRIVÉS D'ACIDE PHÉNYLPROPIONIQUE UTILISÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR GAMMA ACTIVÉ DE LA PROLIFÉRATION DES PEROXISOMES, PROCÉDÉ DE PRÉPARATION DE CEUX-CI ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：DONG A PHARM CO LTD

  公开号：WO2008108602A1

  公开（公告）日：2008-09-12

  [EN] The present invention provides a novel phenylpropionic acid derivative and a PPAR-? modulator comprising the same as an active ingredient. The phenylpropionic acid derivative of the present invention has modulatory action on function of PPAR-? and then exhibits hypoglycemic, hypolipidemic and insulin resistance-reducing effects on PPAR-mediated diseases or disorders. Therefore, the present invention is prophylactically or therapeutically effective for diabetes and metabolic diseases.
  [FR] La présente invention concerne un nouveau dérivé d'acide phénylpropionique et un modulateur du PPAR-? comprenant ledit dérivé en tant qu'ingrédient actif. Le dérivé d'acide phénylpropionique de l'invention présente une action modulatoire sur la fonction du PPAR-? et a par conséquent des effets hypoglycémiques, hypolipidémiques et réducteurs de l'insulinorésistance sur des maladies ou troubles à médiation assurée par le PPAR. Les dérivés de la présente invention s'avèrent être ainsi efficaces d'un point de vue prophylactique ou thérapeutique pour le diabète et les maladies métaboliques.
• Latifolicinin A from a Fermented Soymilk Product and the Structure–Activity Relationship of Synthetic Analogues as Inhibitors of Breast Cancer Cell Growth
  作者：Yi-Yu Ke、Chen-Hsuan Tsai、Hui-Ming Yu、Yu-Chen Jao、Jim-Min Fang、Chi-Huey Wong

  DOI：10.1021/acs.jafc.5b04028

  日期：2015.11.11

  The functional components in soymilk may vary depending upon the fermentation process. A fermented soymilk product (FSP) obtained by incubation with the microorganisms of intestinal microflora was found to reduce the risk of breast cancer. Guided by the inhibitory activities against breast cancer cells, two cytotoxic compounds, daidzein and (S)-latifolicinin A, were isolated from the FSP by repetitive extraction and chromatography. Latifolicinin A is the n-butyl ester of beta-(4-hydroxyphenyl)lactic acid (HPLA). A series of the ester and amide derivatives of (S)-HPLA and L-tyrosine were synthesized for evaluation of their cytotoxic activities. In comparison, (S)-HPLA derivatives exhibited equal or superior inhibitory activities to their L-tyrosine counterparts, and (S)-HPLA amides showed better cytotoxic activities than their corresponding esters. In particular, (S)-HPLA farnesyl amide was active to triple-negative MDA-MB-231 breast cancer cells (IC50 = 27 mu M) and 10-fold less toxic to Detroit-551 normal cells.
• Modulators of peroxisome proliferator activated receptors
  申请人：Brooks Alisa Dawn

  公开号：US20050020684A1

  公开（公告）日：2005-01-27

  Disclosed is a compound represented by Structural Formula (I): Ar is a substituted or unsubstituted aromatic group. Q is a covalent bond, —CH 2 — or —CH 2 CH 2 —; W is a substituted or unsubstituted alkylene or a substituted or unsubstituted heteroalkylene linking group from two to ten atoms in length, preferably from two to seven atoms in length. Phenyl Ring A is optionally substituted with up to four substituents in addition to R 1 and W, R 2 is (CH 2 ) n —CH(OR 2 )—(CH 2 ) n E, —(CH)═C(OR 2 )—(CH 2 ) n E, —(CH 2 ) n —CH(Y)—(CH 2 ) m E or (CH)═C(Y)(CH 2 ) m E; wherein E is COOR 3 , C 1 -C 3 alkylnitrile, carboxamide, sulfonamide, acylsulfonamide or tetrazole and wherein sulfonamide, acylsulfonamide and tetrazole are optionally substituted with one or more substituents independently selected from: C 1 -C 6 alkyl, haloalkyl and aryl-C o - 4 -alkyl; R 2 is H, an aliphatic group, a substituted aliphatic group, haloalkyl, an aromatic group, a substituted aromatic group, —COR 4 , —COOR 4 , —CONR 5 R 6 , —C(S)R 4 , —C(S)OR 4 or C(S)NR 5 R 6 , R 3 is H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. Y is O—, CH 2 —, CH 2 CH 2 — or CH═CH— and is bonded to a carbon atom in Phenyl Ring A that is ortho to R 1 . R 4 -R 6 are independently H, an aliphatic group, a substituted aliphatic group, an aromatic group or a substituted aromatic group. n and m are independently 0, 1 or 2.

  本发明公开了一种由结构式（I）表示的化合物：其中Ar是取代或未取代的芳香基团。Q是共价键，-CH2-或-CH2CH2-; W是取代或未取代的烷基或取代或未取代的异烷基连接基，长度为两到十个原子，优选长度为两到七个原子。苯环A可选地与R1和W以外的最多四个取代基取代，R2是（CH2）n-CH（OR2）-（CH2）nE，-（CH）=C（OR2）-（CH2）nE，-（CH2）n-CH（Y）-（CH2）mE或（CH）=C（Y）（CH2）mE;其中E是COOR3，C1-C3烷基腈，羧酰胺，磺酰胺，酰基磺酰胺或四唑，磺酰胺，酰基磺酰胺和四唑可选地与一个或多个取代基取代，独立地选自：C1-C6烷基，卤代烷基和芳基-Co-4-烷基; R2是H，脂肪基，取代脂肪基，卤代烷基，芳基，取代芳基，-COR4，-COOR4，-CONR5R6，-C（S）R4，-C（S）OR4或C（S）NR5R6，R3是H，脂肪基，取代脂肪基，芳基或取代芳基。Y是O-，CH2-，CH2CH2-或CH═CH-，并与Phenyl环A中与R1相邻的碳原子键合。R4-R6独立地是H，脂肪基，取代脂肪基，芳基或取代芳基。n和m独立地为0、1或2。