CJ-14445 | 35949-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: CJ-14445
• 英文别名: 13,14,15,16-tetranorlabda-7,9(11)-diene-(19,β6),(12,17)-diolide；13,14,15,16-tetranorlabd-7-en-19,6β:12,17-diolide；(3aS,3a(1)R,5aR,10bS)-3a,10b-dimethyl-1,2,3,3a,7,10b-hexahydroisobenzofuro[7,1-fg]isochromene-4,9(3a(1)H,5aH)-dione；(1S,9R,12S,16R)-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7-diene-4,11-dione
• CAS: 35949-19-0
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: CADKOFRWMORBOD-CUBALJKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  CJ-14445 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以85%的产率得到LL-Z1271γ
  参考文献：
  名称：

  An Efficient Synthesis of the Antifungal Dilactone LL-Z1271α and of other Biologically Active Compounds

  摘要：

  DOI：

  10.1016/00404-0399(50)0949d-
• 作为产物：
  描述：

  13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid 在 吡啶 、 silver tetrafluoroborate 、 4 A molecular sieve 、 双氧水 、 碘 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 30.74h， 生成 CJ-14445
  参考文献：
  名称：

  First Synthesis of the Antifungal Oidiolactone C from trans-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds

  摘要：

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.

  DOI：

  10.1021/jo0161882

文献信息

• Total Synthesis of Oidiodendrolides and Related Norditerpene Dilactones from a Common Precursor: Metabolites CJ-14,445, LL-Z1271γ, Oidiolactones A, B, C, and D, and Nagilactone F
  作者：Stephen Hanessian、Nicolas Boyer、Gone Jayapal Reddy、Benoît Deschênes-Simard

  DOI：10.1021/ol901896c

  日期：2009.10.15

  An efficient, high-yielding strategy has been developed for the asymmetric total synthesis of seven norditerpenoid dilactones known for their diverse biological properties. The three key steps employed to obtain a tricyclic lactone intermediate involved a Morita−Baylis−Hillman reaction, the stereocontrolled construction of a γ-lactone through bromolactonization, and an efficient catalytic Reformatsky-type

  已经开发出一种有效，高产的策略，可以不对称地合成七个以其多种生物学特性而闻名的降冰片萜二内酯。用于获得三环内酯中间体的三个关键步骤涉及Morita-Baylis-Hillman反应，通过溴内酯化立体控制γ-内酯的构建以及有效的催化Reformatsky型反应。可以从一个常见的中间体中获得CJ-14,445，LL-Z1271γ，oidiolactones A，B，C和D以及萘基内酯F。通过X射线分析确定结构和立体化学。
• Total syntheses of wentilactones A and B, and related norditerpene dilactones
  作者：Wu Hou、Xin Cao、Peng Xu、Biao Yu

  DOI：10.1039/d2cc04930a

  日期：——

  Wentilactones A and B, two representative tetranorditerpenoid dilactones with promising antitumor activities, are synthesized for the first time. The synthesis employs 3β-hydroxydilactone 6 as a common precursor, which is derived from (S)-Wieland–Miescher ketone, and leads easily to derivatives with various modifications on the A-ring, such as CJ-1445, asperolide B, and the unnamed natural congener

  Wentilactones A 和 B 是首次合成的两种具有抗肿瘤活性的代表性四降二萜双内酯。该合成使用 3β-羟基二内酯6作为常见前体，它衍生自 ( S )-Wieland-Miescher 酮，很容易导致在 A 环上进行各种修饰的衍生物，如 CJ-1445、asperolide B 和未命名的天然同类物4．
• Terpenoid lactone compounds and their production process
  申请人：PFIZER INC.

  公开号：EP0933373A1

  公开（公告）日：1999-08-04

  This invention provides terpenoid lactone compounds, and processes for producing the terpenoid lactone compounds, which comprise cultivating Oidiodedron griseum FERM BP-5778 and then isolating the terpenoid lactone compounds from the fermentation broth. The present invention also provides a pharmaceutical composition comprising the terpenoid lactone compound, which is useful in the treatment of IL-1 and TNF mediated diseases or the like.

  本发明提供了萜类内酯化合物以及生产萜类内酯化合物的工艺，其中包括培养Oidiodedron griseum FERM BP-5778，然后从发酵液中分离出萜类内酯化合物。本发明还提供了一种包含萜类内酯化合物的药物组合物，可用于治疗 IL-1 和 TNF 介导的疾病或类似疾病。
• Enantiospecific syntheses of the potent bioactives nagilactone F and the mould metabolite LL-Z1271α an evaluation of their allelopathic potential
  作者：Alejandro F Barrero、Juan F Sánchez、Jamal Elmerabet、David Jiménez-González、Francisco A Macías、Ana M Simonet

  DOI：10.1016/s0040-4020(99)00355-5

  日期：1999.6

  Improved syntheses are described for nagilactone F and the antibiotic LL-Z1271 alpha, two of the most potent bioactive members of the podolactone family. The allelopathic potential of some members of this podolactone series has been evaluated, with the result that the metabolite LL-Z1271 alpha is one of the most active compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C
  作者：Alejandro F Barrero、José F Quı́lez Del Moral、Juan M Cuerva、E Cabrera、David Jiménez-González

  DOI：10.1016/s0040-4039(00)00815-7

  日期：2000.7

  A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic trifluoroacetates and Pd-catalysed bislactonisation as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.