2-甲氧基-5-(2',3',4'-三甲氧基苯基)环庚三烯酮 | 60423-21-4

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: 2-甲氧基-5-(2',3',4'-三甲氧基苯基)环庚三烯酮
• 英文名称: 2-methoxy-5-(2',3',4'-trimethoxyphenyl)-2,4,6-cycloheptatrien-1-one
• 英文别名: MTC；2-methoxy-5-(2',3',4'-trimethoxyphenyl)tropone；2-methoxy-5-(2,3,4-trimethoxyphenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 60423-21-4
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: QIMGSZURBOTPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2-甲氧基-5-(2',3',4'-三甲氧基苯基)环庚三烯酮 、 sodium thiomethoxide 以 四氢呋喃 、 水 为溶剂， 以72%的产率得到2-Methylsulfanyl-5-(2,3,4-trimethoxy-phenyl)-cyclohepta-2,4,6-trienone
  参考文献：
  名称：

  Discovery of structurally simplified analogs of colchicine as an immunosuppressant

  摘要：

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.007
• 作为产物：
  描述：

  1,2,3-三甲氧基苯 在 palladium diacetate 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 2-甲氧基-5-(2',3',4'-三甲氧基苯基)环庚三烯酮
  参考文献：
  名称：

  Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology

  摘要：

  Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.

  DOI：

  10.1021/jo051636h

文献信息

• Improved and Highly Versatile Synthesis of 5‐Aryltropones
  作者：James Potenziano、Robert Spitale、Mark E. Janik

  DOI：10.1081/scc-200066658

  日期：2005.8.1

  Abstract The use of 5‐iodo‐2‐methoxytropone in palladium(0)‐catalyzed coupling reactions with a variety of arylboronic acids has resulted in significantly improved reaction yields and times for a sterically and electronically diverse series of novel 5‐aryltropones. In addition, the required 5‐iodo‐2‐methoxytropone was conveniently synthesized in excellent yield.

  摘要 5-碘-2-甲氧托酮在钯(0)催化偶联反应中与多种芳基硼酸的使用显着提高了空间和电子多样化系列新型5-芳基托酮的反应产率和时间。此外，所需的 5-碘-2-甲氧托酮可以以优异的收率方便地合成。
• CONJUGATES OF NOSCAPINE AND FOLIC ACID AND THEIR USE IN TREATING CANCER
  申请人：Joshi Harish C.

  公开号：US20110286919A1

  公开（公告）日：2011-11-24

  The present invention is directed to compounds which are conjugates of two non-toxic natural products, noscapine (and various noscapine analogs) and folic acid (and various folic acid analogs), where the folic acid is conjugated to noscapine or the noscapine analog at the 9-position on the isoquinoline ring on the noscapine framework. Pharmaceutical compositions including the compounds, and methods of treating various tumors using the compounds and compositions, are also disclosed. The conjugates are particularly useful for treating cancers which overexpress the Folate Receptor α (FRa) receptor.

  本发明涉及两种非毒性天然产物，诺斯卡平（及各种诺斯卡平类似物）和叶酸（及各种叶酸类似物）的结合物，其中叶酸与诺斯卡平或诺斯卡平类似物在诺斯卡平框架上的异喹啉环的9位结合。还公开了包括该化合物的制药组合物以及使用该化合物和组合物治疗各种肿瘤的方法。这些结合物特别适用于治疗过度表达叶酸受体α（FRa）受体的癌症。
• Synthesis and Characterization of Second Generation Benzofuranone Ring Substituted Noscapine Analogs
  申请人：Aneja Ritu

  公开号：US20140121233A1

  公开（公告）日：2014-05-01

  Compound of Formula (I) and use thereof as microtubule modulating agents in the treatment of cancer are described herein.

  本文描述了化合物I的组合物及其在癌症治疗中作为微管调节剂的用途。
• Delivery systems and methods for noscapine and noscapine derivatives, useful as anticancer agents
  申请人：——

  公开号：US20020137762A1

  公开（公告）日：2002-09-26

  The present invention relates to methods useful for the treatment of neoplastic diseases, tumor cells, and the treatment of cancer delivering compounds of the formula 1 The invention provides various methods of delivering such compounds, combinations of treatments, and altering such compounds to enhance their effectiveness.

  本发明涉及用于治疗肿瘤性疾病、肿瘤细胞和治疗癌症的方法，该方法提供式中的化合物 1 本发明提供了提供此类化合物的各种方法、治疗组合以及改变此类化合物以提高其有效性的方法。
• Nair, Vijay; Powell, Dennis W.; Suri, Suresh Chander, Synthetic Communications, 1987, vol. 17, # 16, p. 1897 - 1900
  作者：Nair, Vijay、Powell, Dennis W.、Suri, Suresh Chander

  DOI：——

  日期：——