Product News | Morpholine in Drug Design

Jan.04.2023

Morpholine is a low-cost organic chemical compound. The six-membered saturated ring contains two two-carbon units, a nitrogen atom and an oxygen atom. This heterocycle features both amine and ether functional groups. Morpholine is basic and the conjugate acid of morpholine has a pKa of about 8.^{1 2} It is also less reactive than typical secondary amines due to the presence of oxygen atom which withdraws electronic density, lowering the nucleophilic character of similar secondary amines.^{2 3}

Morpholine is usually produced through the condensation of ethylene oxide with ammonia, or by the dehydration of diethanolamine with sulfuric acid at high temperature.

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Morpholine is among versatile and efficient synthetic building blocks in medicinal chemistry and pharmacological activities. The heterocyclic motif is an essential component in in the preparation of drugs. This includes marked drugs for the treatment of infectious diseases, tumors, cardiovascular and cerebrovascular diseases, respiratory system diseases, and digestive system diseases.^{3 4}A list of popular therapeutic areas for morpholine based approved drugs can be found here.

There are about nine FDA approved small molecules drugs using morpholine groups approved by FDA in the recent five years. Seven of them are organic heterocyclic drugs, and the other two belong to antisense oligonucleotide. Below is a selective summary of morpholine containing small molecule drugs.

CHEMENU is a professional supplier of organic building blocks, advanced intermediates, and novel synthetic compounds, including morpholine molecules and custom services. Our goal is to support the research programs of global pharmaceutical and biotechnology companies, drug discovery centers, academic institutions, and other research organizations.

For morpholine based building blocks, please visit the specific product section https://www.chemenu.com/category/24.html.

Source:

(1) Vitalii A. Palchykov, Oleksandr Zhurakovskyi. Advances in Heterocyclic Chemistry, Chapter Three - One-pot reactions of three-membered rings giving N,O,S-heterocycles. 2021, Volume 133, Pages 159-223.

(2) Morpholine as ubiquitous pharmacophore in medicinal chemistry: Deep insight into the structure-activity relationship (SAR). Archana Kumari, Rajesh K. Singh. Bioorganic Chemistry. 2020, 96, 103578.

(3) Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies. Kourounakis, AP, Xanthopoulos, D, Tzara, A. ChemMedChem. 2020, 15, 392.

(4) Morpholine as a privileged structure: a review on the medicinal chemistry and pharmacological activity of morpholine containing bioactive molecules. Kourounakis, AP, Xanthopoulos, D, Tzara, A. Med Res Rev. 2020, 40, 709– 752.