3β-hydroxy-pregn-5-en-17β-yl-3'-(p-methoxy)-phenylprop-2'-en-1'-one | 1034000-86-6

• 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: 3β-hydroxy-pregn-5-en-17β-yl-3'-(p-methoxy)-phenylprop-2'-en-1'-one
• 英文别名: 1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1034000-86-6
• 化学式: C₂₉H₃₈O₃
• 分子量: 434.619
• InChiKey: PEGAPZRVEJMUDP-KLRWXFGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-pregn-5-en-17β-yl-3'-(p-methoxy)-phenylprop-2'-en-1'-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 3β-hydroxy-pregn-5-en-17β-yl-5′-(p-methoxyphenyl)-1′-(4′′-phenyl-[1′′,3′′]-thiazol-2′′-yl)-4′,5′-dihydro -1′H-pyrazol-3′- yl
  参考文献：
  名称：

  新型 D 环取代的类固醇 4,5-二氢吡唑噻唑衍生物的设计、合成和分子对接，该衍生物可作为 iNOS/COX-2 抑制剂，对 LPS 诱导的 RAW264.7 巨噬细胞具有有效的抗炎活性。

  摘要：

  炎症是对组织损伤或微生物入侵的重要生物保护反应，被认为是各种生物并发症进展的警报信号。基于先前文献报道证明吡唑和噻唑支架以及氮杂环基化合物对急性和慢性炎症性疾病具有显着功效，我们开发了一组新的新型D环取代的甾体4,5-二氢吡唑噻唑衍生物合成并评价其体外抗炎活性。通过对脂多糖（LPS）诱导的 RAW 264.7 细胞中一氧化氮（NO）释放的抑制活性以及最佳化合物 12b [3β-羟基-pregn-5-en-17β] 进行初步构效关系（SAR）分析。 -基-5'-（邻氯苯基）- 1'-（4''-苯基-[1'', 3'']-噻唑-2''-基） - 4',5'-二氢 - 1 'H-pyrazol - 3'- yl] 比阳性对照治疗甲泼尼龙 (MPS) 表现出更有效的抗炎活性，对 NO 产生的 IC50 值为 2.59 μM，并且对 RAW 264.7 细胞具有较低的细胞毒性。在进一步的机制研究中，

  DOI：

  10.1016/j.jsbmb.2024.106478
• 作为产物：
  描述：

  孕烯醇酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3β-hydroxy-pregn-5-en-17β-yl-3'-(p-methoxy)-phenylprop-2'-en-1'-one
  参考文献：
  名称：

  新型 D 环取代的类固醇 4,5-二氢吡唑噻唑衍生物的设计、合成和分子对接，该衍生物可作为 iNOS/COX-2 抑制剂，对 LPS 诱导的 RAW264.7 巨噬细胞具有有效的抗炎活性。

  摘要：

  炎症是对组织损伤或微生物入侵的重要生物保护反应，被认为是各种生物并发症进展的警报信号。基于先前文献报道证明吡唑和噻唑支架以及氮杂环基化合物对急性和慢性炎症性疾病具有显着功效，我们开发了一组新的新型D环取代的甾体4,5-二氢吡唑噻唑衍生物合成并评价其体外抗炎活性。通过对脂多糖（LPS）诱导的 RAW 264.7 细胞中一氧化氮（NO）释放的抑制活性以及最佳化合物 12b [3β-羟基-pregn-5-en-17β] 进行初步构效关系（SAR）分析。 -基-5'-（邻氯苯基）- 1'-（4''-苯基-[1'', 3'']-噻唑-2''-基） - 4',5'-二氢 - 1 'H-pyrazol - 3'- yl] 比阳性对照治疗甲泼尼龙 (MPS) 表现出更有效的抗炎活性，对 NO 产生的 IC50 值为 2.59 μM，并且对 RAW 264.7 细胞具有较低的细胞毒性。在进一步的机制研究中，

  DOI：

  10.1016/j.jsbmb.2024.106478

文献信息

• Synthesis and evaluation of novel D-ring substituted steroidal pyrazolines as potential anti-inflammatory agents
  作者：Xiaorui Cai、Shulin Zhao、De Cai、Jinhong Zheng、Zhiwei Zhu、Duncan Wei、Zhiwei Zheng、Huide Zhu、Yicun Chen

  DOI：10.1016/j.steroids.2019.03.012

  日期：2019.6

  showed that compound 4g markedly inhibited the expression of pro‐inflammatory factors, including inducible nitric oxide synthase (iNOS), interleukin‐6 (IL‐6), tumour necrosis factor‐&agr; (TNF‐&agr;), and cyclooxygenase‐2 (COX‐2) in LPS‐induced RAW 264.7 cells. These results indicate that derivatives bearing pyrazoline structure might be considered for further research and scaffold optimization in designing

  图形抽象图。没有可用的字幕。亮点合成了新的孕5-烯D环吡唑啉衍生物家族。对所有合成化合物的结构进行了表征。对合成化合物的抗炎生物学活性进行了测定。化合物4g具有优异的抗炎活性和低细胞毒性。摘要 为了鉴定新的潜在抗炎剂，合成了许多具有氮杂环侧链 4a-4l 的新型甾体衍生物，并评估了它们在活化的 RAW 264.7 巨噬细胞中的抗炎作用。合成方案包括两个步骤，第一步是 Claisen-Schmidt 与相应的孕烯醇酮和芳香醛缩合，然后通过 &agr;, &bgr; 亲核加成氨基硫脲。-不饱和羰基作为后续步骤。化合物结构经 1H NMR、13C NMR、HRMS 和 IR 确认。分析这些化合物以测试它们在活化的 RAW 264.7 细胞中的抗炎作用。化合物 4g, 3&bgr;-hydroxy-pregn-5-en-17&bgr;-yl-5'-(m-fluorophenyl)-4', 5'-d
• Synthesis and anti-inflammatory activity of novel steroidal chalcones with 3β-pregnenolone ester derivatives in RAW 264.7 cells in vitro
  作者：Xiaorui Cai、Fei Sha、Chuanyi Zhao、Zhiwei Zheng、Shulin Zhao、Zhiwei Zhu、Huide Zhu、Jiaoling Chen、Yicun Chen

  DOI：10.1016/j.steroids.2021.108830

  日期：2021.7

  identify new potential anti-inflammatory agents, we herein report the synthesis of novel steroidal chalcones with 3β-pregnenolone esters of cinnamic acid derivatives using pregnenolone as the starting material. The structures of the newly synthesised compounds were confirmed by 1H NMR, 13C NMR, HRMS and infrared imaging. All the derivatives were examined to determine their in vitro anti-inflammatory profiles

  为了鉴定新的潜在抗炎剂，我们在此报道了以孕烯醇酮为起始材料，用肉桂酸衍生物的 3β-孕烯醇酮酯合成新型甾体查尔酮。新合成的化合物的结构通过1 H NMR、 13 C NMR、HRMS和红外成像得到证实。对所有衍生物进行了检查，以确定它们对 RAW 264.7 细胞中 LPS 诱导的炎症的体外抗炎特性；根据测量亚硝酸盐水平的格里斯反应，通过定量细胞培养上清液中的促炎介质一氧化氮 (NO) 来评估衍生物，然后进行体外细胞毒性研究。在这些新型衍生物中，化合物11e [3β-3-丙烯酸苯酯-pregn-5-en-17β-yl-3′-(对氟)-苯基丙-2′-en-1′-one]被鉴定为最有效的抗炎剂，通过以剂量依赖性方式抑制 LPS 诱导的促炎介质 NO 表现出显着的抗炎活性，且没有任何细胞毒性。此外，化合物11e显着抑制促炎细胞因子的表达，包括诱导型一氧化氮合酶（iNOS）、白细胞介素-6（IL-
• Pregnenolone derivatives as potential anticancer agents
  作者：M. Iqbal Choudhary、M. Shahab Alam、Atta-ur-Rahman、Sammer Yousuf、Yang-Chang Wu、An-Shen Lin、F. Shaheen

  DOI：10.1016/j.steroids.2011.09.006

  日期：2011.12

  Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring-D modification of 1 resulted in the synthesis of benzylidenes 2-17, pyrazolines 18-76, pyrazoles 85-91, hydrazones 77-84, and oximes 92-107 derivatives. The structure of compound 107 was also deduced through single crystal X-ray diffraction studies. The inclusion of furanyl and pyridyl rings to pregnenolone skeleton increases the cytotoxicity of all compounds significantly. Among benzylidene derivatives, only heterocyclic enone 8 (IC50 = 0.74 mu M/mL against HepG2), and 17 (IC50 = 4.49 mu M/mL against HepG2, IC50 = 5.01 mu M/mL against MDA-MB-230 cancer cell line) exhibited a significant activity. The cytotoxicity data of pyrazoline derivatives 18-76 revealed that only furanyl bearing pyrazolines 40,42-44,48, and 49 exhibited significant activities. While all (O-carboxymethyl) oximes, hydazones, and pyrazoles derivatives of pregnenolone did not show any significant activity against both the cell lines. Thus the furanyl bearing enone 8 (IC50 = 0.74 mu M/mL against HepG2), and its pyrazoline derivative 48 (IC50 = 0.91 mu M/mL against MDA-MB-230 cancer cell lines) were identified as the most active compounds in all derivatives of pregnenolone. (C) 2011 Elsevier Inc. All rights reserved.
• Synthesis antimicrobial and antioxidant studies of new oximes of steroidal chalcones
  作者：Imtiyaz H. Lone、Khaliquz Z. Khan、Bharat I. Fozdar、Fida Hussain

  DOI：10.1016/j.steroids.2013.05.015

  日期：2013.9

  A convenient synthesis of oximes of steroidal chalcones (4a-4j) was performed and structural assignment of the products was confirmed on the basis of IR, (HNMR)-H-1, C-13 NMR, MS and analytical data. The synthesized compounds were screened for in vitro antioxidant activity by using DPPH method and in vitro antimicrobial activity against different bacterial and fungal strains by agar diffusion method. The activity of the tested compounds against each microbe varied due to structural differences between them. Presence and position of different substituents on the benzene ring of the chalconyl pendent had a marked effect on the activity of the compounds. From the results it can be inferred that the compounds 4a-j showed significant antioxidant activity and antimicrobial activity against all microbial strains used for testing. (C) 2013 Elsevier Inc. All rights reserved.
• Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents
  作者：Abid H. Banday、Bilal P. Mir、Imtiyaz H. Lone、K.A. Suri、H.M. Sampath Kumar

  DOI：10.1016/j.steroids.2010.02.014

  日期：2010.12

  An efficient and facile synthesis of 17-pyrazolinyl derivatives of pregnenolone and their evaluation as potential anticancer agents against various human cancer cell lines are reported. The scheme involves the transformation of the starting pregnenolone acetate into pregnenolone, conversion of pregnenolone to the corresponding benzylidine derivatives and finally the conversion of this derivative to the stable steroidal 17-pyrazoline. Various compounds 4b, 4c, 4e, 4f, 4h and 4j showed significant cytotoxic activity especially against HT-29, HCT-15, 502713 cell lines. (C) 2010 Elsevier Inc. All rights reserved.