Deuteration of Heteroarenes Based on DCL™
How Much Do You Know About Heteroarenes?
Heteroarenes are cyclic organic compounds containing at least one heteroatom, the most common heteroatoms being nitrogen, oxygen and sulfur. Heterocyclic systems have attracted considerable attention due to their repeated appearance in many biologically active molecules. Heterocyclic compounds are widely found in natural products, synthetic drugs and functional materials. In terms of natural products, a series of nitrogen-containing heterocyclic compounds represented by alkaloids have rich biological activities, such as vitamin B1, caffeine and nicotine. In the field of medicine, a series of artificially synthesized nitrogen-containing heterocyclic compounds have also become star drugs in the pharmaceutical market, such as chlorpromazine for the treatment of psychosis, captopril for the treatment of hypertension, dilozepam for the treatment of anxiety and insomnia, and isoniazid for the treatment of tuberculosis, etc. In addition, these ring systems have also been found to be the main backbone of many biomolecules, such as hemoglobin, DNA, RNA, vitamins, hormones, etc.
In view of the rich and diverse properties of nitrogen-containing heterocycles and their wide applications, the development of new synthetic strategies for nitrogen-containing heterocycles has always been one of the research hotspots in the field of organic synthesis. Likewise, deuterated derivatives of these heteroarenes have received much attention because their application in mechanistic studies can lead to a better understanding of many synthetic transformations and the development of more efficient reaction conditions.
Fig.1 Selectivity patterns accessed with various HIE methodologies for the labeling of 2-phenylpyridine.[1]
Application of Heteroarenes
Medicinal chemistry
The importance of nitrogen-containing ring systems in medicine cannot be underestimated, and many classes of heterocyclic compounds, including pyrrole, indole, pyridine, pyrrolidine, imidazole, pyrazole, pyrazoline, and lactam, have shown promising therapeutic activity , and can be used as antibacterial, antifungal, anticancer and antidepressant pharmaceutical ingredients in many different fields of pharmacology.
Fig.2 Drugs bearing the indole moiety.[2]
Photosensitive dyes
The introduction of nitrogen-containing heterocycles into the construction of small molecule fluorescent dyes can develop new organelle targeting groups and broaden the development ideas of fluorescent dyes. For example, fluorescent dyes synthesized from quinoxaline and boron ester-substituted coumarin and Nile red through Suzuki reaction have good photostability and cytotoxicity, and can be used as neutral structure mitochondria-targeted fluorescent markers for cell imaging.
Functional fibers
In order to promote the sustainable development of the chemical industry, it is necessary to take the recycling or green degradation of pollutants as one of the core connotations in chemical design. Nitrogen-containing heterocycle-functionalized fibers can not only realize highly selective recognition of environmental pollutant molecules, but also catalyze their green and efficient transformation or degradation, which can provide new ideas for the development of environmentally friendly chemistry.
DCL™ in Deuteration of Heteroarenes
Our DCL™ technology platform realizes the potential for deuteration of heteroarenes, enabling the direct exchange of hydrogen atoms for deuterium atoms in simple steps. To allow for a broad range of labeling possibilities, our toolkit provides access to various modes of selectivity in the deuteration of heteroarenes. Our substrate range includes different nitrogen-containing heteroarenes such as pyridine, tetrahydroquinoline, phenothiazine, phenoxazine, indole, indoline and quinoline, even those with two nitrogen atoms aromatic heteroarenes. We believe our technique will be useful for the preparation of labeled MS standards and deuterated drugs.
Intellectual Property Protection
BOC Sciences has always regarded intellectual property as the most valuable asset of the company and its customers. We have signed non-disclosure agreements with customers and employees before the project starts, and provide synthetic route design and synthesis services in strict accordance with the terms of the non-disclosure agreement, striving to provide customers with target compounds in the shortest time possible.
References
- Chen Pengwei, et al. Progress in Syntheses of Nitrogen-Containing Heterocyclic Compounds Catalyzed by Transition Metals. Chemistry. 2022
- Kopf S, et al. Base‐Mediated Remote Deuteration of N‐Heteroarenes–Broad Scope and Mechanism. European Journal of Organic Chemistry. 2022: e202200204.
- Henary M, et al. Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry. RSC advances. 2020, 10(24): 14170-14197.
