3-((Ξ)-4-dimethylamino-benzylidene)-dihydro-furan-2-one | 58557-39-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-((Ξ)-4-dimethylamino-benzylidene)-dihydro-furan-2-one
• 英文别名: 3-((Ξ)-4-Dimethylamino-benzyliden)-dihydro-furan-2-on；3-[[4-(Dimethylamino)phenyl]methylidene]oxolan-2-one
• CAS: 58557-39-4
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: GQHNDMLBKQUGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((Ξ)-4-dimethylamino-benzylidene)-dihydro-furan-2-one 在 四氢呋喃 、 铂 作用下， 生成 3-(4-dimethylamino-benzyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Substituted γ-Lactones. I. Preparation of α-Substituted γ-Butyrolactones by Condensation of γ-Butyrolactone with Aldehydes. Hydrogenation of the Condensation Products

  摘要：

  DOI：

  10.1021/jo01083a009
• 作为产物：
  描述：

  二氢-3-(三苯基膦亚基)-2(3H)-呋喃酮 、 对二甲氨基苯甲醛 以 二甲基亚砜 为溶剂， 反应 20.0h， 以55.7%的产率得到3-((Ξ)-4-dimethylamino-benzylidene)-dihydro-furan-2-one
  参考文献：
  名称：

  Studies on styrene derivatives. I. Synthesis and antiinflammatory activities of .ALPHA.-benzylidene-.GAMMA.-butyrolactone derivatives.

  摘要：

  两种α-苄叉基-γ-丁内酯，即α-(3, 5-二甲基-4-羟基苄叉基)-γ-丁内酯和α-(3, 5-二叔丁基-4-羟基苄叉基)-γ-丁内酯（KME-4），被发现具有血小板聚集抑制活性；后者还具有强效的抗炎活性，不仅抑制前列腺素合成酶（PGS），还抑制5-脂氧合酶。进一步合成了α-苄叉基-γ-丁内酯，并测试了它们在卡拉胶诱导的大鼠足跖水肿试验（CPE）中的抗炎活性和PGS抑制活性。研究发现，在α-苄叉基-γ-丁内酯中，3位叔丁基、5位烷基和Δ位氧原子的结构组合对发挥抗炎活性是必要的，而且对PGS抑制剂来说，其结构变化非常广泛。在CPE试验中对发挥抗炎活性的结构要求似乎也是对PGS抑制活性的部分要求。

  DOI：

  10.1248/cpb.34.121

文献信息

• Application of ethyl p-methoxycinnamate and derivatives thereof in maintaining self-renewal and pluripotency of stem cells
  申请人：NORTHEAST NORMAL UNIVERSITY

  公开号：US10723998B2

  公开（公告）日：2020-07-28

  Disclosed is a use of ethyl p-methoxycinnamate and derivatives thereof in preparing drugs, culture media, regulating agents or cosmetic and skin caring products for maintaining self-renewal and pluripotency of stem cells. The stem cells comprise adult stem cells, embryonic stem cells and induced pluripotent stem (iPS) cells. Also disclosed is a use of ethyl p-methoxycinnamate and the derivatives thereof in in-vitro amplification of stem cells and preparation of induced pluripotent stem (iPS) cells and a use of ethyl p-methoxycinnamate and the derivatives thereof in preparing drugs for treating cell deletion or injury diseases.

  本发明公开了对甲氧基肉桂酸乙酯及其衍生物在制备药物、培养基、调节剂或美容护肤产品中的用途，用于维持干细胞的自我更新和多能性。干细胞包括成体干细胞、胚胎干细胞和诱导多能干细胞（iPS）。还公开了对甲氧基肉桂酸乙酯及其衍生物在体外扩增干细胞和制备诱导多能干（iPS）细胞中的用途，以及对甲氧基肉桂酸乙酯及其衍生物在制备治疗细胞缺失或损伤疾病药物中的用途。
• APPLICATION OF ETHYL P-METHOXYCINNAMATE AND DERIVATIVES THEREOF IN MAINTAINING SELF-RENEWAL AND PLURIPOTENCY OF STEM CELLS
  申请人：NORTHEAST NORMAL UNIVERSITY

  公开号：US20180195039A1

  公开（公告）日：2018-07-12

  Disclosed is a use of ethyl p-methoxycinnamate and derivatives thereof in preparing drugs, culture media, regulating agents or cosmetic and skin caring products for maintaining self-renewal and pluripotency of stem cells. The stem cells comprise adult stem cells, embryonic stem cells and induced pluripotent stem (iPS) cells. Also disclosed is a use of ethyl p-methoxycinnamate and the derivatives thereof in in-vitro amplification of stem cells and preparation of induced pluripotent stem (iPS) cells and a use of ethyl p-methoxycinnamate and the derivatives thereof in preparing drugs for treating cell deletion or injury diseases.
• Studies on styrene derivatives. I. Synthesis and antiinflammatory activities of .ALPHA.-benzylidene-.GAMMA.-butyrolactone derivatives.
  作者：IKUO KATSUMI、HIDEO KONDO、KATSUJI YAMASHITA、TAKAYOSHI HIDAKA、KAZUNORI HOSOE、TOSHIAKI YAMASHITA、KIYOSHI WATANABE

  DOI：10.1248/cpb.34.121

  日期：——

  Two α-benzylidene-γ-butyrolactones, α-(3, 5-dimethyl-4-hydroxybenzylidene)-γ-butyrolactone and α-(3, 5-di-tert-butyl-4-hydroxybenzylidene)-γ-butyrolactone (KME-4), were found to have platelet aggregation inhibitory activity; the latter also had potent antiinflammatory activity and inhibited not only prostaglandin synthetase (PGS) but also 5-lipoxygenase. Further α-benzylidene-γ-butyrolactones were synthesized, and tested for antiinflammatory activity in carrageenin-induced rat paw edema assay (CPE) and for PGS inhibitory activity. It was found that the structural combination of a tert-butyl group at the 3 position, an alkyl group at the 5 position and an oxygen atom at the Δ position in α-benzylidene-γ-butyrolactone is necessary for antiinflammatory activity, and that rather broad structural variation is possible for inhibitors of PGS. The structural requirements for antiinflammatory activity in the CPE assay also seem to be partial requirements for inhibitory activity against PGS.

  两种α-苄叉基-γ-丁内酯，即α-(3, 5-二甲基-4-羟基苄叉基)-γ-丁内酯和α-(3, 5-二叔丁基-4-羟基苄叉基)-γ-丁内酯（KME-4），被发现具有血小板聚集抑制活性；后者还具有强效的抗炎活性，不仅抑制前列腺素合成酶（PGS），还抑制5-脂氧合酶。进一步合成了α-苄叉基-γ-丁内酯，并测试了它们在卡拉胶诱导的大鼠足跖水肿试验（CPE）中的抗炎活性和PGS抑制活性。研究发现，在α-苄叉基-γ-丁内酯中，3位叔丁基、5位烷基和Δ位氧原子的结构组合对发挥抗炎活性是必要的，而且对PGS抑制剂来说，其结构变化非常广泛。在CPE试验中对发挥抗炎活性的结构要求似乎也是对PGS抑制活性的部分要求。
• Substituted γ-Lactones. I. Preparation of α-Substituted γ-Butyrolactones by Condensation of γ-Butyrolactone with Aldehydes. Hydrogenation of the Condensation Products
  作者：HANS ZIMMER、JOHANNES ROTHE

  DOI：10.1021/jo01083a009

  日期：1959.1