4-[(1E)-3-[3,5-双(1,1-二甲基乙基)苯基]-3-氧-1-丙烯基]苯甲酸 | 110368-33-7

• 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
• 中文名称: 4-[(1E)-3-[3,5-双(1,1-二甲基乙基)苯基]-3-氧-1-丙烯基]苯甲酸
• 英文名称: Ch55
• 英文别名: (E)-4-<3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl>benzoic acid；(E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid；3,5-Di-tert-butylchalcone；4-[(E)-3-(3,5-ditert-butylphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 110368-33-7
• 化学式: C₂₄H₂₈O₃
• 分子量: 364.485
• InChiKey: FOUVTBKPJRMLPE-FMIVXFBMSA-N

物化性质

• 熔点：
  202-203.5 °C
• 沸点：
  509.5±50.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：25mg/mL； DMSO：25mg/mL； DMSO:PBS (pH 7.2) (1:4)：0.2 mg/ml；乙醇：5mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

制备方法与用途

生物活性

Cb5 是一种有效的合成类维生素 A。它与 RAR-α 和 RAR-β 受体具有高亲和力，但对细胞视黄酸结合蛋白 (CRABP) 的亲和力较低。Cb5 能有效诱导 HL60 细胞分化，EC50 值为 200 nM，可用于癌症研究。

靶点

• RARα
• RARβ

体外研究

Cb5 能通过抑制类型 I 转谷氨酰胺酶活性（EC50 = 0.02 nM）和增加胆固醇硫酸盐水平（EC50 = 0.03 nM），抑制兔气管上皮细胞的角质化分化。此外，Cb5 还能诱导胚胎癌 F9 细胞和黑色素瘤 S91 细胞分化（EC50 分别为 0.26 和 0.5 nM），并抑制 3T6 成纤维细胞中精氨酸脱羧酶活性的诱导（EC50 = 1 nM）。

反应信息

• 作为产物：
  描述：

  1-(3,5-二叔丁基苯基)乙酮 、 对甲酰基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 4-[(1E)-3-[3,5-双(1,1-二甲基乙基)苯基]-3-氧-1-丙烯基]苯甲酸
  参考文献：
  名称：

  Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids

  摘要：

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.

  DOI：

  10.1021/jm00124a016

文献信息

• Use of synthetic retinoids for osteopathy
  申请人：HOECHST JAPAN LIMITED

  公开号：EP0619116A2

  公开（公告）日：1994-10-12

  An anti-osteopathic composition comprising as an active ingredient a compound represented by the following formula (I), (II) or (III): which is useful for therapeutic and prophylactic treatment of osteopathia such as osteoporosis and bone fracture.

  一种抗骨病组合物，其活性成分包括下式（I）、（II）或（III）所代表的化合物： 可用于治疗和预防骨质疏松症，如骨质疏松症和骨折。
• Ligands for modulation of orphan receptor-gamma (NR1F3) activity
  申请人：Phenex Pharmaceuticals AG

  公开号：EP2181710A1

  公开（公告）日：2010-05-05

  The invention relates to modulators for the orphan nuclear receptor RORgamma and methods for identification and screening of novel modulators for RORgamma activity as well as methods for treating RORgamma mediated diseases with novel RORgamma modulators identified by such methods.

  本发明涉及孤儿核受体 RORgamma 的调节剂、鉴定和筛选 RORgamma 活性新型调节剂的方法，以及用这种方法鉴定的新型 RORgamma 调节剂治疗 RORgamma 介导的疾病的方法。
• MEDIUM FOR CULTURING STEM CELLS, METHOD FOR CULTURING STEM CELLS, STEM CELL GROWTH PROMOTER, AND CELL COMPOSITION AND METHOD FOR PRODUCING SAME
  申请人：Kyowa Hakko Bio Co., Ltd.

  公开号：EP3511410A1

  公开（公告）日：2019-07-17

  An object of the present invention is to provide a technique for stably, inexpensively, and safely culturing stem cells having a differentiation ability while maintaining an undifferentiated state. The present invention relates to a medium for culturing stem cells, comprising at least one or more compounds selected from the group consisting of a ROCK inhibitor, a PKC inhibitor, a histone methyltransferase inhibitor, and a retinoic acid receptor agonist, and not containing a growth factor or having a low growth factor concentration; a method for culturing stem cells using the medium; a growth promoter for stem cell; as well as a cell composition containing stem cells or differentiated cells therefrom; and a method for producing the cell composition.

  本发明的目的是提供一种技术，稳定、廉价、安全地培养具有分化能力的干细胞，同时保持未分化状态。本发明涉及一种培养干细胞的培养基，该培养基包含至少一种或多种选自 ROCK 抑制剂、PKC 抑制剂、组蛋白甲基转移酶抑制剂和维甲酸受体激动剂的化合物，且不含生长因子或生长因子浓度较低；一种使用该培养基培养干细胞的方法；一种干细胞生长促进剂；以及一种含有干细胞或从中分化的细胞的细胞组合物；以及一种生产该细胞组合物的方法。
• METHOD FOR PRODUCING CARDIOMYOCYTES
  申请人：Kataoka Corporation

  公开号：EP3747993A1

  公开（公告）日：2020-12-09

  The present invention chiefly aims to provide a process for directly inducing cardiomyocytes from somatic cells without performing artificial gene transfer, a cardiomyocyte obtained thereby, and a composition comprising a combination of chemical compounds capable of using for the said process. The present invention can include a process for producing a cardiomyocyte by inducing differentiation directly from a somatic cell, the process comprising a step of culturing the somatic cell in the presence of a MEK inhibitor and a cAMP inducer, and a cardiomyocyte obtained thereby, and then a composition for producing a cardiomyocyte by inducing differentiation directly from a somatic cell, the composition comprising a MEK inhibitor and a cAMP inducer. The cardiomyocytes obtained according to the present invention are useful in regenerative medicine and the like.

  本发明的主要目的是提供一种在不进行人工基因转移的情况下直接从体细胞诱导心肌细胞的工艺、由此获得的心肌细胞以及由能够用于上述工艺的化合物组合而成的组合物。本发明可包括通过直接从体细胞诱导分化产生心肌细胞的工艺，该工艺包括在 MEK 抑制剂和 cAMP 诱导剂存在下培养体细胞的步骤，以及由此获得的心肌细胞，然后是通过直接从体细胞诱导分化产生心肌细胞的组合物，该组合物包括 MEK 抑制剂和 cAMP 诱导剂。根据本发明获得的心肌细胞可用于再生医学等领域。
• METHOD FOR PRODUCING INSULIN-PRODUCING CELLS
  申请人：Kataoka Corporation

  公开号：EP3747994A1

  公开（公告）日：2020-12-09

  The present invention chiefly aims to provide a process for directly inducing insulin-producing cells from somatic cells without performing artificial gene transfer. The present invention can include a process for producing an insulin-producing cell by inducing differentiation directly from a somatic cell, the process comprising a step of culturing the somatic cell in the presence of a cAMP inducer, and six members selected from the group consisting of a GSK3 inhibitor, a TGF-β inhibitor, a BMP inhibitor, a p53 inhibitor, a PI3K inhibitor, a Notch inhibitor and a RAR agonist, or all members thereof. The insulin-producing cells obtained by the present invention are useful in regenerative medicine and the like.

  本发明的主要目的是提供一种在不进行人工基因转移的情况下直接从体细胞诱导胰岛素产生细胞的工艺。本发明可包括通过直接从体细胞诱导分化产生胰岛素产生细胞的工艺，该工艺包括在cAMP诱导剂存在下培养体细胞的步骤，以及选自GSK3抑制剂、TGF-β抑制剂、BMP抑制剂、p53抑制剂、PI3K抑制剂、Notch抑制剂和RAR激动剂或其所有成员组成的组中的六个成员。本发明获得的胰岛素分泌细胞可用于再生医学等领域。