clausine C | 186002-61-9

• 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: clausine C
• 英文别名: clauszoline-L；methyl 7-methoxy-9H-carbazole-3-carboxylate
• CAS: 186002-61-9
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: UHYHEIKZOWURQD-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  454.2±25.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  clausine C 在 三溴化硼 作用下， 以52%的产率得到clausine M
  参考文献：
  名称：

  在有机合成中的过渡金属-第一部分83 ＃：合成和咔唑的药理潜在

  摘要：

  已经使用铁介导的或钯催化的合成方法制备了具有前景的药理学性质的一系列咔唑衍生物。咔唑生物碱咔唑喹啉C，咔唑马杜林A和B，依巴唑啉A和B，新偶氮他汀B和喹他汀A是作为自由基清除剂的抗氧化剂。因此，它们代表了潜在的先导化合物，用于开发针对由氧衍生的自由基引发的疾病的新型药物。由第一个具有抗结核病（TB）活性的天然咔唑生物碱，克劳斯碱K和微茶碱引发，已开展了抗TB活性咔唑衍生物的结构-活性关系研究。6-氧咔唑糖唑啉和糖唑啉对几种微生物显示出抗生素活性。

  DOI：

  10.1007/s00044-007-9073-0
• 作为产物：
  描述：

  9-acetyl-7-methoxy-3-methoxycarbonylcarbazole 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以95%的产率得到clausine C
  参考文献：
  名称：

  Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process

  摘要：

  Carbazoles have attracted great interest in recent years for a variety of applications in organic and medicinal chemistry as well as in materials science. In this work, an efficient method for the synthesis of carbazoles through the intramolecular C-H bond amination of N-substituted 2-amidobiaryls has been developed. Under visible light and an aerobic atmosphere, the transformation requires only catalytic amounts of Pd(OAc)(2) and [Ir(dFppy)(2)phen]PF6 (dFppy = 2-(2,4-difluorophenyl)pyridine; phen = 1,10-phenanthroline), the latter of which is utilized in synthetic chemistry for the first time. Spectroscopic and electrochemical studies revealed that the reaction is initiated by photoinduced electron transfer from a palladacyclic intermediate, formed from the 2-amidobiaryl and Pd-II species, to the photoexcited Ir catalyst. This step triggers reductive elimination in a Pd-III-containing palladacycle to produce the carbazole and a Pd-I species. The one-electron-reduced photocatalyst is reoxidized by O-2 to generate the original form of the photocatalyst, and the Pd-I species can be oxidized to the resting state through oxidative electron transfer to O-2 or the excited-state photocatalyst.

  DOI：

  10.1021/acscatal.5b00817

文献信息

• Mastering tricyclic ring systems for desirable functional cannabinoid activity
  作者：Ravil R. Petrov、Lindsay Knight、Shao-Rui Chen、Jim Wager-Miller、Steven W. McDaniel、Fanny Diaz、Francis Barth、Hui-Lin Pan、Ken Mackie、Claudio N. Cavasotto、Philippe Diaz

  DOI：10.1016/j.ejmech.2013.09.038

  日期：2013.11

  Compound 64 had potent inhibitory effects on pain hypersensitivity in a rat model of neuropathic pain. Other potent and CB2 receptor–selective compounds, including compounds 63 and 68, and a selective CB1 agonist, compound 74 were also discovered. In addition, we identified the CB2 ligand 35 which failed to promote CB2 receptor internalization and inhibited compound CP55,940-induced CB2 internalization despite

  人们对使用大麻素受体 2 (CB2) 激动剂治疗神经性疼痛和其他适应症越来越感兴趣。为了继续我们正在进行的旨在开发新的小分子大麻素配体的计划，我们合成了一系列新型咔唑和 γ-咔啉衍生物。新合成的化合物的亲和力通过对人 CB2 大麻素受体和大鼠 CB1 大麻素受体的竞争性放射性配体置换试验确定。使用受体内化和 [ 35 S] GTP-γ-S 测定法表征对人 CB1 和 CB2 受体的功能活性和选择性。咔唑系列的构效关系和优化研究导致发现了非选择性 CB1 和 CB2 激动剂，化合物4. 我们随后为提高该先导化合物的 CB2 选择性所做的研究工作导致了 CB2 选择性化合物64的发现，该化合物可强力内化 CB2 受体。在神经性疼痛的大鼠模型中，化合物64对疼痛超敏反应具有强效抑制作用。还发现了其他有效的 CB2 受体选择性化合物，包括化合物63和68，以及选择性 CB1 激动剂，化合物74。此外，我们还鉴定了
• Novel Tricyclic Modulators of Cannabinoid Receptors
  申请人：Diaz Philippe

  公开号：US20120039804A1

  公开（公告）日：2012-02-16

  The compounds of the invention are modulators of cannabinoid receptors CB1 or CB2. The compounds can be used for the prevention or treatment of, e.g., pain, cancer, skin diseases, weight-associated disorders, chemical addictions, psychiatric disorders, neurodegenerative disorders, bone diseases, and inflammatory diseases. The compounds of the invention can further be used to study these diseases and disorders, as well as cannabinoid receptor biology, by coupling the compounds to, e.g., imaging agents.

  该发明的化合物是大麻素受体CB1或CB2的调节剂。这些化合物可用于预防或治疗疼痛、癌症、皮肤疾病、与体重相关的疾病、化学成瘾、精神障碍、神经退行性疾病、骨疾病和炎症性疾病等。该发明的化合物还可用于研究这些疾病和障碍，以及大麻素受体生物学，方法是将这些化合物与成像剂等耦合。
• Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
  作者：Gary L. Points、Christopher M. Beaudry

  DOI：10.1021/acs.orglett.1c02449

  日期：2021.9.3

  Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a

  取代咔唑由 3-triflato-2-pyrones 和炔基苯胺有效构建。咔唑上可耐受多个取代基，并观察到对区域化学的完全控制。产生了复杂且空间拥挤的替代模式。该策略也用于制备取代的联咔唑和相关联芳基。最后，该方法在咔唑天然产物 clausine C 的合成中得到展示。
• Palladium-Catalyzed Intramolecular C-H Amination in Water
  作者：Lizheng Yang、Hao Li、Haifei Zhang、Hongjian Lu

  DOI：10.1002/ejoc.201601043

  日期：2016.12

  found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2 as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic

  发现钯 (II) 催化对水中的分子内 C-H 胺化有效。以 2-叠氮联苯为底物，该反应有效地提供了各种咔唑，N2 作为唯一的副产物。该反应显示出高官能团耐受性，可用于合成多种天然咔唑生物碱。催化过程受水促进，在所研究的有机溶剂中反应效率低下。
• Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon–Carbon/Carbon–Nitrogen Bond-Forming Reactions
  作者：Toshiki Akiyama、Yuki Wada、Makito Yamada、Yasunori Shio、Tetsuo Honma、Shuhei Shimoda、Kazuki Tsuruta、Yusuke Tamenori、Hitoshi Haneoka、Takeyuki Suzuki、Kazuo Harada、Hayato Tsurugi、Kazushi Mashima、Jun-ya Hasegawa、Yoshihiro Sato、Mitsuhiro Arisawa

  DOI：10.1021/acs.orglett.0c02574

  日期：2020.9.18

  Self-assembled multilayer iron(0) nanoparticles (NPs, 6–10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon–carbon/carbon–nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal–nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1

  自组装多层铁（0）纳米颗粒（NPs，6-10 nm），即硫改性的金负载的Fe（0）[SAFe（0）]，被开发用于无配体的一锅碳-碳/碳氮键形成反应。SAFe（0）是使用成熟的金属-纳米颗粒催化剂制备方案通过同时原位金属NP和带有1,4-双（三甲基甲硅烷基）-1,4-二氢吡嗪（Si -DHP）的纳米空间组织（PSSO）成功制备的作为强还原剂。SAFe（0）易于在空气中处理，并且可以在反应循环中以低铁浸出率进行回收。