bromoeudistamin D | 101927-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: bromoeudistamin D
• 英文别名: 7-Bromo-eudistomine D；5,7-dibromo-9H-pyrido[3,4-b]indol-6-ol
• CAS: 101927-49-5
• 化学式: C₁₁H₆Br₂N₂O
• 分子量: 341.989
• InChiKey: UNIUKKWPGRGSRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C (decomp)
• 沸点：
  474.3±40.0 °C(Predicted)
• 密度：
  2.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bromoeudistamin D 生成 (5,7-dibromo-9H-pyrido[3,4-b]indol-6-yl) acetate
  参考文献：
  名称：

  KOBAYASI, DZYUNITI;ISIBASI, MASAKI;OIDZUMI, YASUSI

  摘要：

  DOI：
• 作为产物：
  描述：

  6-Methoxy-9H-pyrido<3,4-b>indol 在 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 bromoeudistamin D
  参考文献：
  名称：

  Eudistomin derivatives, novel phosphodiesterase inhibitors: synthesis and relative activity

  摘要：

  描述了新型磷酸二酯酶抑制剂的制备，包括8-乙酰氧基-5-碘-6-甲氧基吡咯[3,4-b]吲哚、5,7-二溴-6-羟基吡咯[3,4-b]吲哚、5,7-二氯-6-羟基吡咯[3,4-b]-吲哚和8-乙酰氧基-5-溴-6-甲氧基吡咯[3,4-b]吲哚，以及对环磷酸腺苷磷酸二酯酶产生50％的抑制浓度，即分别为3×10−6、3×10−6、7×10−6和1×10−5 M。通过与其他无活性的欧地菲啶及其衍生物的化学结构进行比较，讨论了这些欧地菲啶衍生物的相对效力。

  DOI：

  10.1111/j.2042-7158.1988.tb05154.x

文献信息

• Structure-Activity Relationships for the Ca2+-releasing Activity of 6-Hydroxy-β-carboline Analogues in Skeletal Muscle Sarcoplasmic Reticulum—The Effects of Halogen Substitution at C-5 and C-7
  作者：Asami Seino-Umeda、Masami Ishibashi、Jun'Ichi Kobayashi、Yasushi Ohizumi

  DOI：10.1211/0022357001774309

  日期：2010.2.18

  10(-4) M, respectively, indicating that these analogues are 10-200 times more potent than caffeine. Substitution of bromine by chlorine or iodine at the C-5 and C-7 positions markedly reduced the activity of the analogues with a methyl group at the N-9 position. These results suggest that halogens at the C-5 and C-7 positions in the beta-carboline skeleton are essential for Ca2+-releasing activity and that

  对6-羟基-β-咔啉类似物的结构-活性关系的研究是在定量测量骨骼肌皮肤纤维的肌浆网中Ca 2+释放活性的基础上进行的。在C-5和C-7位置将卤素取代为氢，然后将甲基进一步引入6-羟基-β-咔啉的N-9位置，导致Ca2 +释放活性。50％有效浓度的5,7-二溴大黄素D，5,7-二氯大黄素D，5,7-二碘大黄素D，9-甲基-5,7-二溴大黄素D，9-甲基-5,7-二氯大黄素D，9 -methyl-5,7-diiodoeudistomin D和咖啡因分别为5.6 x 10（-6），6.3 x 10（-6），7.8 x 10（-6），2.1 x 10（-6），2.0 x 10（- 5），3.7 x 10（-5）和4.7 x 10（-4）M，表明这些类似物的效力比咖啡因强10-200倍。在C-5和C-7位置用氯或碘取代溴显着降低了在N-9位置带有甲基的类似物的活性。这些结果表明，β-咔啉骨架中C-5和C-7位的卤素对于Ca2
• Isolation and use of ryanodine receptors
  申请人：E. I. du Pont de Nemours and Company

  公开号：EP2380899A1

  公开（公告）日：2011-10-26

  The genes encoding ryanodine receptor homologs have been characterized from multiple insect families including lepidopteran tobacco budworm (Heliothis virescens), homopteran green peach aphid (Myzus persicae), corn plant hopper (Peregrinus maidis), cotton melon aphid (Aphis gossypii) and fruitfly (Drosophila melanogaster). The full-length genes have been isolated, cloned and amplified in bacterial cells. Expression in insect cells shows that the recombinant protein folds into a functional calcium release channel. The genes and their corresponding polypeptides have a number of uses including, but not limited to, the isolation of other pest ryanodine receptors, the development of screens to identify insecticidally active compounds, use of fragments of genes as pesticides, fragments of protein for antibody production, fragments of protein for determination of the structure of insecticide binding sites, and identification of insecticides that disrupt the calcium balance in cells through other messengers that interact with the receptor calcium release mechanism. Methods are outlined for overcoming toxic effects of expressing recombinant proteins in host cells.

  编码雷诺丁受体同源物的基因来自多个昆虫家族，包括鳞翅目烟草芽虫（Heliothis virescens）、同翅目绿桃蚜（Myzus persicae）、玉米植株跳虫（Peregrinus maidis）、棉瓜蚜（Aphis gossypii）和果蝇（Drosophila melanogaster）。全长基因已在细菌细胞中分离、克隆和扩增。在昆虫细胞中的表达显示，重组蛋白折叠成一个功能性钙释放通道。这些基因及其相应的多肽有许多用途，包括但不限于分离其他害虫的雷诺丁受体、开发筛选出具有杀虫活性的化合物、将基因片段用作杀虫剂、将蛋白质片段用于抗体生产、将蛋白质片段用于确定杀虫剂结合位点的结构，以及确定通过与受体钙释放机制相互作用的其他信使破坏细胞内钙平衡的杀虫剂。还概述了克服在宿主细胞中表达重组蛋白的毒性效应的方法。
• Expression system for toxic ion channels, in particular ryanodine receptors
  申请人：E. I. du Pont de Nemours and Company

  公开号：EP2383280A1

  公开（公告）日：2011-11-02

  The genes encoding ryanodine receptor homologs have been characterized from multiple insect families including lepidopteran tobacco budworm (Heliothis virescens), homopteran green peach aphid (Myzus persicae), corn plant hopper (Peregrinus maidis), cotton melon aphid (Aphis gossypii) and fruitfly (Drosophila melanogaster). The full-length genes have been isolated, cloned and amplified in bacterial cells. Expression in insect cells shows that the recombinant protein folds into a functional calcium release channel. The genes and their corresponding polypeptides have a number of uses including, but not limited to, the isolation of other pest ryanodine receptors, the development of screens to identify insecticidally active compounds, use of fragments of genes as pesticides, fragments of protein for antibody production, fragments of protein for determination of the structure of insecticide binding sites, and identification of insecticides that disrupt the calcium balance in cells through other messengers that interact with the receptor calcium release mechanism. Methods are outlined for overcoming toxic effects of expressing recombinant proteins in host cells.

  编码雷诺丁受体同源物的基因来自多个昆虫家族，包括鳞翅目烟草芽虫（Heliothis virescens）、同翅目绿桃蚜（Myzus persicae）、玉米植株跳虫（Peregrinus maidis）、棉瓜蚜（Aphis gossypii）和果蝇（Drosophila melanogaster）。全长基因已在细菌细胞中分离、克隆和扩增。在昆虫细胞中的表达显示，重组蛋白折叠成一个功能性钙释放通道。这些基因及其相应的多肽有许多用途，包括但不限于分离其他害虫的雷诺丁受体、开发筛选出具有杀虫活性的化合物、将基因片段用作杀虫剂、将蛋白质片段用于抗体生产、将蛋白质片段用于确定杀虫剂结合位点的结构，以及确定通过与受体钙释放机制相互作用的其他信使破坏细胞内钙平衡的杀虫剂。还概述了克服在宿主细胞中表达重组蛋白的毒性效应的方法。
• Method of identifying insulin secretion stimulating compounds, and the use of such compounds in treating insulin-secretion related disorders
  申请人：——

  公开号：US20030148259A1

  公开（公告）日：2003-08-07

  Calcium Induced Calcium Release (CICR) in &bgr;-cells has been found to be a novel target for stimulating insulin secretion in a glucose-dependent manner. The present invention relates to a method of identifying compounds that stimulate insulin secretion in a context-dependent manner based on the finding that compounds stimulating insulin secretion in a glucose-dependent manner are able to elicit periodic amplified Ca 2+ release in &bgr;-cells. The invention also relates to the use of such compounds, for the manufacture of a medicament for use in the treatment of defective insulin secretion related disorders, especially type 2 diabetes.

  研究发现，&bgr;-细胞中的钙诱导钙释放（CICR）是以葡萄糖依赖方式刺激胰岛素分泌的新靶点。本发明涉及一种鉴别化合物的方法，这种化合物能以环境依赖性方式刺激胰岛素分泌，其依据是发现以葡萄糖依赖性方式刺激胰岛素分泌的化合物能够引起周期性放大的 Ca 2&plus； 细胞中释放。本发明还涉及使用此类化合物制造药物，用于治疗与胰岛素分泌缺陷有关的疾病，特别是 2 型糖尿病。
• Eudistomins A-Q, .beta.-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum
  作者：Kenneth L. Rinehart、Junichi Kobayashi、Gary C. Harbour、Jeremy Gilmore、Mark Mascal、Tom G. Holt、Lois S. Shield、Francoise Lafargue

  DOI：10.1021/ja00245a031

  日期：1987.5