青霉素 | 55303-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 青霉素
• 英文名称: 1'(S)-penicillide
• 英文别名: vermixocin A；penicillide；pencillide；6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one
• CAS: 55303-92-9
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: UOWGLBYIKHMCIS-HNNXBMFYSA-N

物化性质

• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	penicillide monomethyl ether	54962-05-9	C22H26O6	386.445
  ——	3-(1-Hydroxy-3-methylbutyl)-11-(1-methyl-ethoxy)-4-methoxy-9-methyl-7H-dibenzo[b,g][1,5]dioxocin-5-one	——	C24H30O6	414.499
  ——	8-Chloro-11-hydroxy-3-((S)-1-hydroxy-3-methyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one	689224-86-0	C21H23ClO6	406.863
  ——	11-hydroxy-4-methoxy-9-methyl-3-(3-methylbutanoyl)-5H,7H-dibenzo[b,g][1,5]-dioxocin-5-one	134564-56-0	C21H22O6	370.402
  ——	7-bromo-9-chloro-6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one	689224-55-3	C21H22BrClO6	485.759

反应信息

• 作为反应物：
  描述：

  青霉素 在 N-氯代丁二酰亚胺 、 三氯化铁 作用下， 以 乙醇 为溶剂， 以84%的产率得到8-Chloro-11-hydroxy-3-((S)-1-hydroxy-3-methyl-butyl)-4-methoxy-9-methyl-7H-6,12-dioxa-dibenzo[a,d]cycloocten-5-one
  参考文献：
  名称：

  Dibenzodioxocinones—A new class of CETP inhibitors

  摘要：

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.073

文献信息

• Circulation-active dibenzo[1,5]dioxocin-5-ones
  申请人：Bayer Aktiengesellschaft

  公开号：US05089487A1

  公开（公告）日：1992-02-18

  Cardioactive compounds of the formula ##STR1## in which R.sup.1 and R.sup.8 and R.sup.14 and R.sup.15 can be hydrogen or various organic radicals.

  该化合物的心脏活性化合物的公式为##STR1## 其中R.sup.1和R.sup.8和R.sup.14和R.sup.15可以是氢或各种有机基团。
• 7H-dibenzo[b,g][1,5]dioxocin-5-one derivatives and use thereof
  申请人：Bischoff Hilmar

  公开号：US20060247303A1

  公开（公告）日：2006-11-02

  The present invention relates to substituted 7H-dibenzo[b,g][1,5]dioxocin-5-one-derivatives, to processes for their preparation and to their use in medicaments, in particular as inhibitors of the cholesterol ester transfer protein (CETP) for the treatment and/or prevention of cardiovascular disorders, in particular hypolipoproteinaemia, dyslipidaemias, hypertriglyceridaemias, hyperlipidaemias and arteriosclerosis.

  本发明涉及取代的7H-二苯并[b，g][1,5]二氧杂环戊烷-5-酮衍生物，其制备过程以及它们在药物中的应用，特别是作为胆固醇酯转移蛋白（CETP）的抑制剂，用于治疗和/或预防心血管疾病，特别是低脂蛋白血症，脂质代谢异常，高三酰甘油血症，高脂血症和动脉硬化。
• Penicillanthone and penicillidic acids A–C from the soil-derived fungus Penicillium aculeatum PSU-RSPG105
  作者：Charuwan Daengrot、Vatcharin Rukachaisirikul、Kwanruthai Tadpetch、Souwalak Phongpaichit、Kawitsara Bowornwiriyapan、Jariya Sakayaroj、Xu Shen

  DOI：10.1039/c6ra04401h

  日期：——

  (penicillanthone, 1) and three new diphenyl ether derivatives (penicillidic acids A–C, 2–4) together with 14 known compounds (5–18) were isolated from the soil-derived fungus Penicillium aculeatum PSU-RSPG105. The structures were elucidated by spectroscopic analyses. The absolute configuration of compound 1 was determined using the Snatzke's method whereas those of compounds 2–4 was established by comparison

  从土壤真菌绿脓青霉PSU-RSPG105中分离了一个新的x吨酮（青霉烯酮，1）和三个新的二苯醚衍生物（青霉酸A–C，2-4）以及14种已知化合物（5–18）。通过光谱分析阐明了结构。化合物1的绝对构型是使用Snatzke方法确定的，而化合物2-4的绝对构型是通过将其旋光度与结构相关化合物的旋光度进行比较来确定的。化合物5显示出对结核分枝杆菌的温和抗分枝杆菌活性，MIC值为25μgmL -1对非癌性Vero细胞无细胞毒性。此外，altenusin（12）对耐甲氧西林的金黄色葡萄球菌表现出中等的抗菌活性，MIC值为32μgmL -1，对Vero细胞的活性较弱，IC 50值为19.46μM。
• Azaphilone and Diphenyl Ether Derivatives from a Gorgonian-Derived Strain of the Fungus <i>Penicillium pinophilum</i>
  作者：Dong-Lin Zhao、Chang-Lun Shao、Qiang Zhang、Kai-Ling Wang、Fei-Fei Guan、Ting Shi、Chang-Yun Wang

  DOI：10.1021/acs.jnatprod.5b00575

  日期：2015.9.25

  Three new azaphilone derivatives, pinophilins D-F (1-3), and one new diphenyl ether derivative, hydroxypenicillide (10), together with nine known compounds (4-9, 11-13), were isolated from the gorgonian-derived fungus Penicillium pinophilum XS-20090E18. Their structures including absolute configurations were determined by spectroscopic data, chemical conversions, the ECD exciton chirality method, and ECD calculations. Compounds 10-13 exhibited inhibitory activity against the larval settlement of the barnacle Balanus amp hitrite at nontoxic concentrations. Compounds 10 and 11 showed cytotoxicity against Hep-2, RD, and HeLa cell lines.
• Dibenzodioxocinones—A new class of CETP inhibitors
  作者：David Brückner、Frank-Thorsten Hafner、Volkhart Li、Carsten Schmeck、Joachim Telser、Alexandros Vakalopoulos、Gabriele Wirtz

  DOI：10.1016/j.bmcl.2005.05.073

  日期：2005.8

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.