含羞草霉素 | 59493-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 含羞草霉素
• 英文名称: mimosamycin
• 英文别名: 7-methoxy-2,6-dimethyl-3,5,8(2H)isoquinolinetrione；mimosamycine；mimosamysin；7-methoxy-2,6-dimethyl-2H-isoquinoline-3,5,8-trione；7-methoxy-2,6-dimethylisoquinoline-3,5,8-trione
• CAS: 59493-94-6
• 化学式: C₁₂H₁₁NO₄
• 分子量: 233.224
• InChiKey: BXQZTMMXFKFJIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  含羞草霉素 生成 2,5-Dihydroxy-3-methoxy-4-methyl-6-prop-2-enylbenzonitrile
  参考文献：
  名称：

  CASTEEL, DEE ANN;PARKER, KATHLYN A., ABSTR. PAP. 194TH ACS NAT. MEET. (AMER. CHEM. SOC.), NEW ORLEANS, LA, AUG+

  摘要：

  DOI：
• 作为产物：
  描述：

  jorunnamycin A 在 4-二甲氨基吡啶 、 selenium(IV) oxide 、 对甲苯磺酸 、 silver nitrate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 15.0h， 生成 含羞草霉素
  参考文献：
  名称：

  Chemistry of renieramycins. Part 6: Transformation of renieramycin M into jorumycin and renieramycin J including oxidative degradation products, mimosamycin, renierone, and renierol acetate

  摘要：

  The transformation of remeramycin M (1m) into renieramycin J (1j) and jorumycin (2) is presented along with the results of antiproliferative assay data. The chemical stability and the oxidative degradation of 2 and renieramycm E (1e) to generate simple isoquinoline alkaloids, such as mimosamycin (7), renierol acetate (12), and renierone (8) are also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.071

文献信息

• Synthesis of Mimosamycin
  作者：Bart Kesteleyn、Norbert De Kimpe

  DOI：10.1021/jo990767d

  日期：2000.2.1

  regioselective introduction of a chloromethyl group at C-6 and a methoxycarbonylmethyl group at C-5 and subsequent reaction of the intermediate methyl (o-(chloromethyl)phenyl)acetate derivative 16 with methylamine. Oxidation of the 5,7,8-trimethoxy-2,6-dimethyl-1, 4-dihydroisoquinoline-3(2H)-one 17 thus obtained, using cerium(IV) ammonium nitrate as a selective oxidizing agent, gave mimosamycin (1) in good overall

  通过在C-6处氯甲基和C-5处甲氧基羰基甲基的区域选择性引入，由八步合成Mimosamycin（1），由2-甲氧基-3-甲基-1,4-苯醌合成总收率为13％。中间体（邻-（氯甲基）苯基）乙酸甲酯衍生物16与甲胺的随后反应。使用硝酸铈（IV）铵作为选择氧化剂，氧化得到的5,7,8-三甲氧基-2,6-二甲基-1,4-二氢异喹啉-3（2H）-one 17，得到咪莫霉素（1 ）的整体产量。
• Chemistry of Antitumor Isoquinoline-quinone Alkaloids: Unexpected Oxidative Degradation of Saframycin S to Generate Simple Isoquinoline Alkaloids, Mimosamycin and Mimocin
  作者：Naoki Saito、Yu-ichi Koizumi、Chieko Tanaka、Khanit Suwanborirux、Surattana Amnuoypol、Akinori Kubo

  DOI：10.3987/com-03-s45

  日期：——

  Saframycin S, prepared by treating saframycin A with silver nitrate in aqueous acetonitrile, was transformed into simple isoquinolinequinones, mimosamycin and mimocin, by treatment with a catalytic amount of trifluoroacetic acid (TFA) in chloroform. The proposed mechanism for this oxidative degradation is presented.

  用硝酸银在乙腈水溶液中处理 saframycin A 制备的 Saframycin S 通过在氯仿中用催化量的三氟乙酸 (TFA) 处理转化为简单的异喹啉醌、含羞草霉素和 mimocin。提出了这种氧化降解的拟议机制。
• Cribrostatins 1 and 2
  申请人：ARIZONA BOARD OF REGENTS

  公开号：EP0528615A1

  公开（公告）日：1993-02-24

  The blue marine sponge Cribrochalina sp., collected in the Republic of the Maldives, was found to contain the new cell growth inhibitory isoquinolinequinones designated cribrostatin 1 (8.8 x 10⁻⁶% yield) and 2 (3.1 x 10¹⁶% yield) which are active against the P388 lymphocytic leukemia cell line (PS ED₅₀ 1.58 µg/mL, PS ED₅₀ 2.73 µg/mL, respectively). Importantly, both cribrostatins 1 and 2 have shown selective activity against all of the nine human melanoma cell lines employed by the U.S. National Cancer Institute. Structural determinations of both substances were accomplished utilizing high field NMR (400 MHz) and mass spectral studies. Confirmation of the cribrostatin 1 structure was achieved by X-ray crystallographic techniques.

  在马尔代夫共和国采集的蓝色海洋海绵 Cribrochalina sp、在马尔代夫共和国采集到的蓝色海洋海绵 Cribrochalina sp.1 x 10¹⁶% 收率），对 P388 淋巴细胞白血病细胞株具有活性（PS ED₅₀ 1.58 µg/mL，PS ED₅₀ 2.73 µg/mL）。重要的是，核前列素 1 和核前列素 2 对美国国家癌症研究所使用的所有九种人类黑色素瘤细胞系都具有选择性活性。这两种物质的结构测定是通过高场核磁共振（400 MHz）和质谱研究完成的。X 射线晶体学技术确认了 Cribrostatin 1 的结构。
• Conjugate heat shock protein-binding peptides
  申请人：——

  公开号：US20030134787A1

  公开（公告）日：2003-07-17

  The present invention relates (i) to conjugate peptides engineered to noncovalently bind to heat shock proteins; (ii) to compositions comprising such conjugate peptides, optionally bound to heat shock protein; and (iii) to methods of using such compositions to induce an immune response tin a subject in need of such treatment. It is based, at least in part, on the discovery of tethering molecules which may be used to non-covalently link antigenic peptides to heat shock proteins. The present invention also provides for methods of identifying additional tethers which may be comprised, togethter with antigenic sequences, in conjugate peptides.

  本发明涉及(i)工程化的与热休克蛋白非共价结合的共轭肽；(ii)包含这种共轭肽的组合物，可选择与热休克蛋白结合；以及(iii)使用这种组合物诱导需要这种治疗的受试者产生免疫反应的方法。本发明至少部分基于系链分子的发现，该分子可用于将抗原肽与热休克蛋白非共价连接。本发明还提供了鉴定其它系链的方法，这些系链可与抗原序列一起组成共轭多肽。
• Modulation of heat-shock-protein-based immunotherapies
  申请人：——

  公开号：US20040071656A1

  公开（公告）日：2004-04-15

  Methods and compositions are provided for modulating the immune response to an antigen based upon the finding that the cell surface protein CD40 is a mammalian heat shock protein (hsp) receptor. Cell surface CD40 mediates the binding, cell signaling, and uptake of hsp and particularly hsp with antigen bound thereto. Methods are provided for modulating hsp-antigen uptake and an immune response to the antigen by altering CD40 expression, as well as utilizing CD40-binding fragments of mammalian hsp and muteins thereof for targeting antigens to CD40-expressing cells. Screening methods for agonists and antagonists of the CD40-hsp interaction are also provided.

  根据细胞表面蛋白 CD40 是哺乳动物热休克蛋白（hsp）受体这一发现，提供了调节对抗原的免疫反应的方法和组合物。细胞表面 CD40 介导 hsp，特别是与抗原结合的 hsp 的结合、细胞信号传导和吸收。本研究提供了通过改变 CD40 表达来调节 hsp 抗原吸收和对抗原的免疫反应的方法，以及利用哺乳动物 hsp 的 CD40 结合片段及其静音素将抗原靶向 CD40 表达细胞的方法。还提供了 CD40-hsp 相互作用的激动剂和拮抗剂的筛选方法。

表征谱图