Tri-O-acetyl-alkannin

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Tri-O-acetyl-alkannin
• 英文别名: [4-Acetyloxy-3-(1-acetyloxy-4-methylpent-3-enyl)-5,8-dioxonaphthalen-1-yl] acetate；[4-acetyloxy-3-(1-acetyloxy-4-methylpent-3-enyl)-5,8-dioxonaphthalen-1-yl] acetate
• 化学式: C₂₂H₂₂O₈
• 分子量: 414.412
• InChiKey: AGEUQIWKOYUHBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-甲基-3-戊烯酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 四溴化碳 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.49h， 生成 Tri-O-acetyl-alkannin
  参考文献：
  名称：

  A New Efficient Route for Multigram Asymmetric Synthesis of Alkannin and Shikonin

  摘要：

  A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, a selective and high yielding deprotection protocol furnishes the title compounds as pure crystalline precipitates. Thus, a multigram synthesis of shikonin, alkannin and shikalkin is achieved in high yield and enantioselectivity.

  DOI：

  10.1002/1521-3765(20020415)8:8<1795::aid-chem1795>3.0.co;2-v

文献信息

• Monocyte modulation and control of tumor metastasis
  申请人：La Jolla Institute for Allergy and Immunology

  公开号：US11053297B2

  公开（公告）日：2021-07-06

  Disclosed herein are methods of increasing numbers of monocytes to a tumor or cancer metastasis site in a subject. Non-limiting embodiments include administering or using a Nur77 polypeptide or subsequence thereof; a Nur77 agonist; a CX3CR1 agonist; CD14+ CD16+ monocytes and/or CD14dimCD16+ (CD115+CD11b+ GR1− (Ly6C−)) monocytes; CD14+ CD16+ monocytes and/or CD14dimCD16+ (CD115+CD11b+GR1− (Ly6C−)) monocytes contacted with a Nur77 agonist or contacted with a CX3CR1 agonist. Also disclosed herein are methods of increasing, stimulating, activating or promoting monocyte migration to or mobilization against a tumor or cancer metastasis in a subject. Non-limiting embodiments include administering a Nur77 polypeptide or subsequence thereof; a Nur77 agonist; a CX3CR1 agonist; CD14+ CD16+ monocytes and/or CD14dimCD16+ (CD115+CD11b+GR1− (Ly6C−)) monocytes; or CD14+ CD16+ monocytes and/or CD14dimCD16+ (CD115+CD11b+GR1− (Ly6C−)) monocytes contacted with a Nur77 agonist or contacted with a CX3CR1 agonist.

  本文公开了增加受试者肿瘤或癌症转移部位单核细胞数量的方法。非限制性实施方案包括给药或使用 Nur77 多肽或其子序列；Nur77 激动剂；CX3CR1 激动剂；CD14+ CD16+ 单核细胞和/或 CD14dimCD16+ (CD115+CD11b+ GR1- (Ly6C-))单核细胞；与 Nur77 激动剂接触或与 CX3CR1 激动剂接触的 CD14+ CD16+ 单核细胞和/或 CD14dimCD16+ (CD115+CD11b+GR1- (Ly6C-))单核细胞。本文还公开了增加、刺激、激活或促进单核细胞向受试者的肿瘤或癌症转移灶迁移或动员的方法。非限制性实施方案包括施用 Nur77 多肽或其子序列；Nur77 激动剂；CX3CR1 激动剂；CD14+ CD16+ 单核细胞和/或 CD14dimCD16+ (CD115+CD11b+GR1- (Ly6C-))单核细胞；或与 Nur77 激动剂接触或与 CX3CR1 激动剂接触的 CD14+ CD16+ 单核细胞和/或 CD14dimCD16+ (CD115+CD11b+GR1- (Ly6C-))单核细胞。
• METHODS AND USES OF NUR77 AND NUR77 AGONISTS TO MODULATE MACROPHAGES AND MONOCYTES, AND TREAT INFLAMMATION, INFLAMMATORY DISEASE AND CARDIOVASCULAR DISEASE
  申请人：LA JOLLA INSTITUTE FOR ALLERGY AND IMMU

  公开号：US20130108602A1

  公开（公告）日：2013-05-02

  Methods of decreasing, reducing, inhibiting, suppressing, limiting or controlling an undesirable or aberrant immune response, immune disorder, inflammatory response, or inflammation in a subject; decreasing, reducing, inhibiting, suppressing, limiting or controlling an autoimmune response, disorder or disease in a subject; and decreasing, reducing, inhibiting, suppressing, limiting or controlling an adverse cardiovascular event or cardiovascular disease in a subject, are provided. Methods include, for example, administering a Nur77 polypeptide or subsequence thereof, a Nur77 agonist, or CD14 + CD16 + monocytes or CD14 dim CD16 + (CD115 + CD11b + GR1 − (Ly6C−)) monocytes or macrophages to a subject to decrease, reduce, inhibit, suppress, limit or control the underlying condition or an adverse symptom or pathology of the condition.
• MONOCYTE MODULATION AND CONTROL OF TUMOR METASTASIS
  申请人：La Jolla Institute for Allergy and Immunology

  公开号：US20180312568A1

  公开（公告）日：2018-11-01

  Disclosed herein are methods of increasing numbers of monocytes to a tumor or cancer metastasis site in a subject. Non-limiting embodiments include administering or using a Nur77 polypeptide or subsequence thereof; a Nur77 agonist; a CX3CR1 agonist; CD14+ CD16 + monocytes and/or CD14dimCD16 + (CD115 + CD11b + GR1 − (Ly6C−)) monocytes; CD14 + CD16 + monocytes and/or CD14dimCD16 + (CD115 + CD11b + GR1 − (Ly6C−)) monocytes contacted with a Nur77 agonist or contacted with a CX3CR1 agonist. Also disclosed herein are methods of increasing, stimulating, activating or promoting monocyte migration to or mobilization against a tumor or cancer metastasis in a subject. Non-limiting embodiments include administering a Nur77 polypeptide or sub-sequence thereof; a Nur77 agonist; a CX3CR1 agonist; CD14+ CD16+ monocytes and/or CD14dimCD16 + (CD115 + CD11b + GR1 − (Ly6C−)) monocytes; or CD14 + CD16 + monocytes and/or CD14dimCD16 + (CD115 + CD11b + GR1 − (Ly6C−)) monocytes contacted with a Nur77 agonist or contacted with a CX3CR1 agonist.