17-(3-dimethylaminoacryloyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one | 1032963-24-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17-(3-dimethylaminoacryloyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• 英文别名: 17-(3-(dimethylamino)acryloyl)androst-4-ene-3-one
• CAS: 1032963-24-8
• 化学式: C₂₄H₃₅NO₂
• 分子量: 369.547
• InChiKey: BEAHNRQRJJSFMM-OCCJOITDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17-(3-dimethylaminoacryloyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one 在 哌啶 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 17-(ethyl 3-amino-thieno[2,3-b]pyridine-2-carboxylate)androst-4-ene-3-one
  参考文献：
  名称：

  The effect of newly synthesized progesterone derivatives on apoptotic and angiogenic pathway in MCF-7 breast cancer cells

  摘要：

  Due to its high potency and selectivity, anticancer agents consisting of combined molecules have gained great interests. The current study introduces newly synthesized progesterone derivatives of promising anticancer effect. Moreover, the pro-apoptotic and anti-angiogenic effects of these compounds were studied extensively. Several thiazole, pyridine, pyrazole, thiazolopyridine and pyrazolopyridine progesterone derivatives were synthesized. The structure of the novel progesterone derivatives was elucidated and confirmed using the analytical and spectral data. This novel derivatives were tested for their cytotoxic effect against human breast cancer cells (MCF-7) using neutral red uptake assay. Tested compounds showed anticancer activity against MCF-7 cancer cell line in the descending order of 7 > 2 > 3 > 8 > 6 > 9 > 4. The expression levels of Bcl-2, survivin, CCND1, CDC2, P53 and P21, VEGF, Hif-1 alpha, MMP-2, MMP-9, Ang-1, Ang-2, and FGF-1 genes were investigated using QRT-PCR (Quantitative real time-polymerase chain reaction). The study clarified that compounds 2, 3, 4, 6, 7, 8 and 9 showed significant pro-apoptotic effect through the down regulation of Bcl-2., besides, survivin and CCND1 expression levels were down regulated by compounds 3, 4, 6, 7, 8, 9. However, Compound 4 may exert this pro-apoptotic effect through the up-regulation of P53 gene expression. On the other hand, the anti-angiogenic effect of these newly synthesized derivatives was due to their down regulation of VEGF, Ang-2, MMP-9 and FGF-1; and the up-regulation of HIF-1 alpha and ang-1. This study recommended promising pro-apoptotic and antiangiogenic anticancer agents acting through the regulation of key regulators of apoptosis, cell cycle genes, and pro-angiogenic genes.

  DOI：

  10.1016/j.steroids.2017.08.002
• 作为产物：
  描述：

  黄体酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 xylene 为溶剂， 反应 20.0h， 以75%的产率得到17-(3-dimethylaminoacryloyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  甾族杂环衍生物的新途径：具有生物活性的吡唑基和异恶唑基戊二烯衍生物的合成

  摘要：

  吡唑基和异恶唑基戊二烯衍生物是由适当的酰氯和羟肟基氯与烯胺基孕酮衍生物合成的。通过元素分析，光谱数据和化学转化来阐明新合成的化合物。对某些产品进行了针对某些细菌和某些真菌植物病原体的测试

  DOI：

  10.1002/jhet.5570440102

文献信息

• Nickel‐Catalyzed Tandem Ring Contraction of TEMPO and C−N Bond Transamination of Enaminones toward Amino Diversity of Enaminones
  作者：Haozhi Wu、Tian Luo、Jie‐Ping Wan、Jianwen Jiang、Yunyun Liu

  DOI：10.1002/ejoc.202200552

  日期：2022.7.14

  The Ni(II)-catalyzed ring contraction in TEMPO providing 2,3-dimethyl pyrrolidine as well as the capture of this species with N,N-dimethyl enaminones through transamination are realized for the practical synthesis of 2,3-dimethyl pyrrolidine functionalized enaminones for the first time.

  在 TEMPO 中 Ni(II) 催化的环收缩提供 2,3-二甲基吡咯烷，以及通过氨基转移用N,N-二甲基烯胺酮捕获该物种，实现了 2,3-二甲基吡咯烷官能化烯胺酮的实际合成首次。
• Electrochemical enaminone C–H thiolation/C–N amination cascade for thiazole synthesis and its diastereoselective dearomatization
  作者：Haijin Guo、Yunyun Liu、Chengping Wen、Jie-Ping Wan

  DOI：10.1039/d2gc01644c

  日期：——

  An electrochemical method for the synthesis of 2-aminothiazoles via aryl ring construction using enaminones and thioureas is reported. The cascade enamine C–H thiolation and C–N amination constitutes a major transformation for the thiazole ring formation. Moreover, a simple modification of electrochemical conditions enables the tunable dearomatization of the thiazole ring via vicinal dialkoxylation

  报道了一种使用烯胺酮和硫脲通过芳环结构合成 2-氨基噻唑的电化学方法。级联烯胺 C-H 硫醇化和 C-N 胺化构成噻唑环形成的主要转变。此外，对电化学条件的简单修改能够通过连位二烷氧基化对噻唑环进行可调节的脱芳构化，从而合成具有优异非对映选择性的具有季碳中心的 4,5-二烷氧基噻唑啉。
• Unlock the C–N Bond Amidation of Enaminones: Metal-Free Synthesis of Enamides by Water-Assisted Transamidation
  作者：Haozhi Wu、Kang Chen、Yunyun Liu、Jie-Ping Wan

  DOI：10.1021/acs.joc.3c01926

  日期：2024.1.5

  The C–N bond transamidation of primary amides with N,N-dimethyl enaminones has been efficiently realized by heating in the presence of trifluoromethanesulfonic acid (TfOH). The method enables the practical synthesis of valuable enamides without the use of any metal reagent. In addition, this transamidation protocol can also be expanded to the reactions of sulfonamides, and the late-stage functionalization

  通过在三氟甲磺酸（TfOH）存在下加热，可以有效地实现伯酰胺与N , N-二甲基烯胺的 C-N 键转酰胺基反应。该方法能够在不使用任何金属试剂的情况下实际合成有价值的烯酰胺。此外，该转酰胺基化方案还可以扩展到磺胺类药物的反应，并且在塞来考昔、伐地考昔等磺胺类药物上的后期功能化已经得到验证。此外，通过使用D 2 O的同位素标记实验已经确定了水参与辅助转酰胺基化过程，这为设计其他转酰胺基化反应的催化策略提供了新的可能性。
• Tunable Trifunctionalization of Tertiary Enaminones for the Regioselective and Metal-Free Synthesis of Discrete and Proximal Phosphoryl Nitriles
  作者：Zhongrong Xu、Leiqing Fu、Xia Fang、Bin Huang、Liyun Zhou、Jie-Ping Wan

  DOI：10.1021/acs.orglett.1c01581

  日期：2021.7.2