Dihydroabietinsaeure | 503299-01-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Dihydroabietinsaeure
• 英文别名: Dihydropalustric acid；(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,5,6,7,8,9,10,10a-decahydrophenanthrene-1-carboxylic acid
• CAS: 503299-01-2
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: OEILFLGOGZTONZ-HXTIDPMASA-N

物化性质

• 沸点：
  422.5±34.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dihydroabietinsaeure 在 氯化亚砜 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 12.5h， 生成 (1R,4aS,10aR)-N-((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)carbamothioyl)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthrene-1-carboxamide
  参考文献：
  名称：

  苯并菲结构的不对称二取代酰基硫脲的合成及抗肿瘤活性

  摘要：

  一系列具有氢菲结构稠合的新颖不对称二取代acylthioureas由来自Δ合成8 -dihydroabietic和脱氢松香酸分别。它们的结构通过IR，1 H-和13 C-NMR光谱表征。通过MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物）方法评估标题化合物对SMMC7721和A549肿瘤细胞的抗肿瘤活性。结果表明，三种化合物（4C1，4D1和4D2）抗SMMC7721和A549细胞，其表现出的IC高度有效的活动50SMMC7721细胞的值分别在1.87–12.67μM和A549细胞的2.20–6.79μM之间。这表明该acylthioureas呋喃基与稠合Δ结构-活性关系8 -dihydroabietyl基，三羟甲基稠合与Δ 8 -dihydroabietyl和脱氢松香可以产生增强这种针对SMMC7721和A549细胞的化合物的活性。

  DOI：

  10.1007/s00044-010-9303-8

文献信息

• New hypocholesterolemic abietamide derivatives. I. Structure-activity relationship.
  作者：YUKIO FUJITA、KENJI SEMPUKU、KOJI KITAGUCHI、TAMIKI MORI、HIROMU MURAI、YOSHIAKI YOSHIKUNI、HIROSHI ENOMOTO、ROLAND LOSER

  DOI：10.1248/cpb.28.453

  日期：——

  Various amides of tetrahydroabietic, Δ8-dihydroabietic, abietic and dehydroabietic acids were prepared and tested for hypocholesterolemic activity in cholesterol-fed rats. The introduction of an aromatic ring into the amine moiety of secondary amides markedly enhanced the activity of the parent acids. The secondary amides having an aliphatic ring were slightly less active than those having an aromatic ring, but those having an alkyl or allyl group were completely inactive. Tetrahydroabietic and dihydroabietic acids appear to be preferable (in terms of activity) to abietic or dehydroabietic acid as the acid moiety of these amide derivatives. N-Phenyltetrahydro (18)- or N-phenyl-Δ8-dihydroabietamide (19) and N-benzyltetrahydro (20)- or N-benzyl-Δ8-dihydroabietamide (21) are considered to be promising parent compounds for potent hypocholesterolemic drugs. In the case of benzyl derivatives of Δ8-dihydroabietamide, N-(4-methoxybenzyl)-Δ8-dihydroabietamide (49) and N-(α-benzylbenzyl)-Δ8-dihydroabietamide (58) were the most active, being more than 10 times as potent as the corresponding parent compounds.

  制备了四氢阿比特酸、Δ8-二氢阿比特酸、阿比特酸和去氢阿比特酸的各种酰胺，并在喂养胆固醇的大鼠中测试其降胆固醇活性。在次级酰胺的氨基部分引入芳香环显著增强了母酸的活性。具有烷烃环的次级酰胺活性略低于那些具有芳香环的酰胺，而具有烷基或烯丙基的酰胺则完全不活跃。四氢阿比特酸和二氢阿比特酸似乎比阿比特酸或去氢阿比特酸更优越（就活性而言）作为这些酰胺衍生物的酸部分。N-苯基四氢阿比特酸（18）或N-苯基-Δ8-二氢阿比特酸酰胺（19）以及N-苄基四氢阿比特酸（20）或N-苄基-Δ8-二氢阿比特酸酰胺（21）被认为是具有潜力的有效降胆固醇药物的母体化合物。在Δ8-二氢阿比特酸酰胺的苄基衍生物中，N-(4-甲氧基苄基)-Δ8-二氢阿比特酸酰胺（49）和N-(α-苄基苄基)-Δ8-二氢阿比特酸酰胺（58）是最活跃的，其活性超过对应母体化合物的10倍以上。
• Synthesis and antitumor activities of unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure
  作者：Xiao-Ping Rao、Yong Wu、Zhan-Qian Song、Shi-Bin Shang、Zong-De Wang

  DOI：10.1007/s00044-010-9303-8

  日期：2011.4

  A series of novel unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure were synthesized from Δ8-dihydroabietic and dehydroabietic acid, respectively. Their structures were characterized by IR, 1H-, and 13C-NMR spectroscopy. The antitumor activities of the title compounds against SMMC7721 and A549 tumor cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium

  一系列具有氢菲结构稠合的新颖不对称二取代acylthioureas由来自Δ合成8 -dihydroabietic和脱氢松香酸分别。它们的结构通过IR，1 H-和13 C-NMR光谱表征。通过MTT（3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物）方法评估标题化合物对SMMC7721和A549肿瘤细胞的抗肿瘤活性。结果表明，三种化合物（4C1，4D1和4D2）抗SMMC7721和A549细胞，其表现出的IC高度有效的活动50SMMC7721细胞的值分别在1.87–12.67μM和A549细胞的2.20–6.79μM之间。这表明该acylthioureas呋喃基与稠合Δ结构-活性关系8 -dihydroabietyl基，三羟甲基稠合与Δ 8 -dihydroabietyl和脱氢松香可以产生增强这种针对SMMC7721和A549细胞的化合物的活性。