3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)-1-propanone | 178445-85-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)-1-propanone
• 英文别名: 1-(3-Hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)propan-1-one；3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)propan-1-one
• CAS: 178445-85-7
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: UFGUGWUCWSJYBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)-1-propanone 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-3-benzo[1,3]dioxol-5-yl-1-(3-carboxymethoxy-phenyl)-propyl ester
  参考文献：
  名称：

  Synthesis and activity of bivalent FKBP12 ligands for the regulated dimerization of proteins

  摘要：

  The total synthesis and in vitro activities of a series of chemical inducers of dimerization (CIDs) is described. The use of small-molecule CIDs to control the dimerization of engineered FKBP12-containing fusion proteins has been demonstrated to have broad utility in biological research as well as potential medical applications in gene and cell therapies. The facility and flexibility of preparation make this new class of wholly synthetic compounds exceptionally versatile tools for the study of intracellular signaling events mediated by protein-protein interactions or protein localization. While some congeners possess potency comparable to or better than the first generation natural product-derived CID, FK1012, structure-activity relationships are complex and underscore the need for application-specific compound optimizations. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00125-4
• 作为产物：
  描述：

  (2E)-3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以41%的产率得到3-(1,3-benzodioxol-5-yl)-1-(3-hydroxyphenyl)-1-propanone
  参考文献：
  名称：

  Synthesis and activity of bivalent FKBP12 ligands for the regulated dimerization of proteins

  摘要：

  The total synthesis and in vitro activities of a series of chemical inducers of dimerization (CIDs) is described. The use of small-molecule CIDs to control the dimerization of engineered FKBP12-containing fusion proteins has been demonstrated to have broad utility in biological research as well as potential medical applications in gene and cell therapies. The facility and flexibility of preparation make this new class of wholly synthetic compounds exceptionally versatile tools for the study of intracellular signaling events mediated by protein-protein interactions or protein localization. While some congeners possess potency comparable to or better than the first generation natural product-derived CID, FK1012, structure-activity relationships are complex and underscore the need for application-specific compound optimizations. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00125-4

文献信息

• [EN] SYNTHETIC DERIVATIVES OF RAPAMYCIN AS MULTIMERIZING AGENTS FOR CHIMERIC PROTEINS WITH IMMUNOPHILIN-DERIVED DOMAINS<br/>[FR] DERIVES SYNTHETIQUES DE RAPAMYCINE UTILISES COMME AGENTS DE MULTIMERISATION DE PROTEINES CHIMERES A DOMAINES DERIVES DE L'IMMUNOPHILINE
  申请人：ARIAD GENE THERAPEUTICS, INC.

  公开号：WO1997031898A1

  公开（公告）日：1997-09-04

  (EN) New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formula (I): M-L-Q, a resolved stereoisomer thereof or mixture of one or more such stereoisomers, and pharmaceutically acceptable salts thereof, wherein M is an immunophilin-binding group comprising a moiety of formula (II); G is independently selected from the group consisting of (a), (b), and (c); Q comprises a moiety of formula (II), a naturally occurring macrocyclic FKBP ligand or derivative thereof, or is a synthetic FKBP ligand of formula (III); n = 1 or 2; X = O, NH or CH2; B1 and B2 are independently H or aliphatic, heteroaliphatic, aryl or heteroaryl; Y = O, S, NH, -NH(C=O)-, -NH(C=O)-O-, -NH(SO2)- or NR3, or represents a covalent bond from R2 to carbon 9; R1, R2, and R3 are the same or different and are independently aliphatic, heteroaliphatic, aryl or heteroaryl; and, L is a linker moiety covalently linking monomers M to Q or covalently linking M1 to M2 through covalent bonds to either R1, R2, not necessarily the same in each of M1 and M2.(FR) L'invention concerne de nouveaux composés de multimérisation d'immunophilines et des protéines contenant de l'immunophiline ou des domaines apparentés à l'immunophiline. Les composés ont la formule (I) M-L-Q, un de leur stéréoisomère résolu ou un mélange d'un ou de plusieurs de ces stéréoisomères, et leurs sels pharmaceutiquement acceptables, formule dans laquelle M représente un groupe de liaison d'immunophiline comprenant une fraction de la formule (II) dans laquelle G est choisi indépendamment dans le groupe constitué de (a, b, c), Q comprend une fraction de formule (II), un ligand FKBP macrocyclique naturel ou un dérivé de celui-ci, ou bien un ligand FKBP synthétique de formule (III) dans lesquelles n = 1 ou 2; X = O, NH ou CH2; B1 and B2 représentent indépendamment H ou aryle ou hétéroaryle aliphatique, hétéroaliphatique; Y = O, S, NH, -NH(C=O)-, -NH(C=O)-O, -NH(SO2)- ou NR3, ou il représente une liaison covalente de R2 à l'atome de carbone 9, R1, R2, et R3 sont identiques ou différents et représentent indépendamment aryle ou hétéroaryle aliphatique, hétéroaliphatique, et L représente une fraction de liaison liant de manière covalente des monomères M à Q ou liant de manière covalente M1 à M2 par des liaisons covalentes à soit R1 soit R2, non nécessairement identiques dans chacun de M1 et M2.

  (中) 揭示了用于多聚免疫蛋白和含有免疫蛋白或免疫蛋白相关域的蛋白质的新化合物。该化合物的化学式为(I): M-L-Q，其已解析立体异构体或一个或多个此类立体异构体的混合物以及其药学上可接受的盐。其中，M是一个免疫蛋白结合基团，包括式(II)的基团；G独立地选择自(a)、(b)和(c)组成的群体；Q包括式(II)的基团、自然存在的大环FKBP配体或其衍生物，或式(III)的合成FKBP配体；n=1或2；X=O、NH或CH2；B1和B2独立地是H或脂肪族、杂脂族、芳基或杂芳基；Y=O、S、NH、-NH(C=O)-、-NH(C=O)-O-、-NH(SO2)-或NR3，或代表从R2到碳9的共价键；R1、R2和R3相同或不同，独立地是脂肪族、杂脂族、芳基或杂芳基；L是一个连接单体M到Q的连接基团，或通过共价键将M1与M2连接起来，通过共价键连接到R1或R2，M1和M2中的每个不一定相同。
• Synthetic multimerizing agents
  申请人：——

  公开号：US20030036654A1

  公开（公告）日：2003-02-20

  New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formula M—L—Q where M is a synthetic ligand for an FKBP protein

  本发明披露了一种用于多聚免疫蛋白和含有免疫蛋白或免疫蛋白相关结构域的蛋白质的新化合物。该化合物的公式为M—L—Q，其中M是FKBP蛋白的合成配体。
• Synthetic Multimerizing Agents
  申请人：Holt Dennis A.

  公开号：US20120130076A1

  公开（公告）日：2012-05-24

  New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formula M-L-Q where M is a synthetic ligand for an FKBP protein.

  新化合物被披露用于多聚免疫蛋白和含有免疫蛋白或免疫蛋白相关域的蛋白质。这些化合物的化学式为M-L-Q，其中M是FKBP蛋白的合成配体。
• NEW MULTIMERIZING AGENTS
  申请人：ARIAD GENE THERAPEUTICS, INC.

  公开号：EP0776327A1

  公开（公告）日：1997-06-04
• EP0776327A4
  申请人：——

  公开号：EP0776327A4

  公开（公告）日：1997-12-10