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Oxadiazoles
Oxadiazoles are a class of heterocyclic aromatic chemical compound of the azole family; with the molecular formula C2H2N2O. There are four isomers of oxadiazole: File:1,2,3-oxadiazole.svg, 1,2,3-oxadiazole File:1,2,4-oxadiazole.svg, 1,2,4-oxadiazole File:1,2,5-oxadiazole.svg, 1,2,5-oxadiazole(furazan) File:1,3,4-oxadiazole.svg, 1,3,4-oxadiazole 1,2,4-Oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole are all known and appear in a variety of pharmaceutical drugs including raltegravir, butalamine, fasiplon, oxolamine, and pleconaril. The 1,2,3-isomer is unstable and ring-opens to form the diazoketone tautomer; however, it does exist within the unusual sydnone motif. In 2018, a compound called bis(1,2,4-oxadiazole)bis(methylene) dinitrate which might have a 1.5 times the power of TNT was developed at the United States Army Research Laboratory (ARL) working with the Los Alamos National Laboratory Los Alamos National Laboratory (often shortened as Los Alamos and LANL) is one ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,3,4-Oxadiazole
1,3,4-Oxadiazole is a nitrogen and oxygen containing heterocycle, and one of the four isomers of oxadiazole. Derivatives 1,3,4-Oxadiazole itself is not commonly used in organic chemistry, but many of its derivative (chemistry), derivatives are important. For example, raltegravir is an HIV drug which contains an 1,3,4-oxadiazole ring. Other pharmaceutical drugs containing the 1,3,4-oxadiazole ring include fenadiazole, zibotentan, and tiodazosin. 1,3,4-Oxadiazole derivatives can be synthesized in a variety of ways. One pathway is from oxidation of tetrazoles in the presence of aldehydes. Similarly, the reaction of tetrazoles with acyl chlorides provides oxadiazoles. Both methods involve the release of N2. See also *Furazan (1,2,5-oxadiazole) References [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oxolamine
Oxolamine is a cough suppressant that is available as a generic drug in many jurisdictions. Oxolamine also has anti-inflammatory activity, which causes a reduction in irritation of the nerve receptors of the respiratory tract. It is mainly used for the treatment of pharyngitis, tracheitis, bronchitis, bronchiectasis and pertussis Whooping cough, also known as pertussis or the 100-day cough, is a highly contagious bacterial disease. Initial symptoms are usually similar to those of the common cold with a runny nose, fever, and mild cough, but these are followed by two or t .... Oxolamine is not approved in the USA, it may be marketed elsewhere internationally as a cough suppressant. It is listed as a prescription drug in New Zealand legislation. Oxolamine is also approved in Taiwan for the treatment of respiratory tract inflammation. References Antitussives Oxadiazoles Diethylamino compounds {{respiratory-system-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bis-oxadiazole
Bis-oxadiazole, or more formally known as bis(1,2,4-oxadiazole)bis(methylene) dinitrate, is a nitrated heterocyclic compound of the oxadiazole family. Bis-oxadiazole is related to bis-isoxazole tetranitrate (BITN), which was developed at the United States Army Research Laboratory (ARL). With a high nitrogen content, these compounds are poised to release a large volume of very stable N2. It is a “melt-cast” explosive material that is potentially both more powerful and environmentally friendly alternative to TNT. Synthesis Glyoxal condenses with hydroxylamine to yield diaminoglyoxime (DAG). Treating DAG with methyl glycolate in the presence of base at high temperature yields bis(1,2,4-oxadiazole). Replacement for TNT TNT is attractive explosive because it is a melt-castable. A low melting point of about 80 °C and high decomposition temperature of 295 °C allows manufacturers to safely pour TNT into molds. The production of TNT generates hazardous waste, e.g. re ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Furazan
Furazan, or 1,2,5-oxadiazole, is a heterocyclic aromatic organic compound consisting of a five-atom ring containing 1 oxygen and 2 nitrogen atoms. The furazan ring system is also found in the steroid furazabol. Furazan and its derivatives are obtained from the oxime derivatives of 1,2-diketones. Synthesis In theory the simplest means of producing furazan is the cyclic-dehydration of glyoxime (the di- oxime of glyoxal), however the instability of furazan to high temperature or extremes of pH requires that this process be performed carefully. The formation of furazan from glyoxime is also exothermic and takes place with the copious evolution of noxious gases. The reaction may be achieved by heating glyoxime to 150 °C in the presence of succinic anhydride; furazan will evaporate at this temperature and thus is continuously removed from the reaction mixture. Derivatives ;3,4-Dimethylfurazan 3,4-Dimethylfurazan ( b.p. 154–159 °C) is prepared by an analogous process by ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Raltegravir
Raltegravir, sold under the brand name Isentress, is an antiretroviral medication used, together with other medication, to treat HIV/AIDS. It may also be used, as part of post exposure prophylaxis, to prevent HIV infection following potential exposure. It is taken by mouth. Common side effects include trouble sleeping, feeling tired, nausea, high blood sugar, and headaches. Severe side effects may include allergic reactions including Stevens–Johnson syndrome, muscle breakdown, and liver problems. It is unclear if use during pregnancy or breastfeeding is safe. Raltegravir is an HIV integrase strand transfer inhibitor which blocks the functioning of HIV integrase which is needed for viral replication. Raltegravir was approved for medical use in the United States in 2007. It is on the World Health Organization's List of Essential Medicines. Lamivudine/raltegravir, a combination with lamivudine, is also available. Medical uses Raltegravir was initially approved only for use ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Butalamine
Butalamine is a vasodilator. Synthesis Check with imolamine (alternate nitrogen reacts) The halogenation of benzamidoxime 32-90-1 22-31-1(1) with chlorine and subsequent reaction with cyanamide Cyanamide is an organic compound with the formula C N2 H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a ... (3) gives 5-amino-3-phenyl-1,2,4-oxadiazole 663-37-4(4). Base catalyzed alkylation with dibutylaminoethyl chloride 3422-90-7(5) completes the synthesis of butalamine (6). References Vasodilators Oxadiazoles {{cardiovascular-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fasiplon
Fasiplon (RU 33203) is a nonbenzodiazepine anxiolytic drug from the imidazopyrimidine family of drugs. Fasiplon binds strongly to benzodiazepine sites on the GABAA receptor and has similar anxiolytic effects in animals, but with less sedative or muscle relaxant action. It was developed by a team at Roussel Uclaf Roussel Uclaf S.A. was a French pharmaceutical company and one of several predecessor companies of today's Sanofi. It was the second largest French pharmaceutical company before it was acquired by Hoechst AG of Frankfurt, Germany in 1997, with p ... in the 1990sUS Patent 5869481 Anticonvulsive 1-ar(alk)ylimidazolin-2-ones and process for making References {{GABAAR PAMs Sedatives Imidazopyrimidines Oxadiazoles GABAA receptor positive allosteric modulators ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sydnone
Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position. Like other mesoionic compounds they are di-polar, possessing both positive and negative charges which are delocalized across the ring. Recent computational studies have indicated that sydnones and other similar mesoionic compounds are nonaromatic, "though well-stabilized in two separate regions by electron and charge delocalization." Sydnones are heterocyclic compounds named after the city of Sydney, Australia. A sydnone imine in which the keto group of sydnone (=O) has been replaced with an imino (=NH) group can be found as a substructure in the stimulant drugs feprosidnine and mesocarb. Discovery Sydnone was first prepared in 1935 by Earl & Mackney by cyclodehydration of N-Nitroso- N-phenylglycine with acetic anhydride. Later work showed that this could be applied fairly generally to the nitrosamines of N-substituted amino acids. Chemical struc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pleconaril
Pleconaril (Picovir) is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in patients exposed to picornavirus respiratory infections. Pleconaril, administered either orally or intranasally, is active against viruses in the ''Picornaviridae'' family, including '' Enterovirus'' and '' Rhinovirus''. It has shown useful activity against the dangerous enterovirus D68. History Pleconaril was originally developed by Sanofi-Aventis, and licensed to ViroPharma in 1997. ViroPharma developed it further, and submitted a New Drug Application to the United States Food and Drug Administration (FDA) in 2001. The application was rejected, citing safety concerns; and ViroPharma re-licensed it to Schering-Plough in 2003. The Phase II clinical trial was completed in 2007. A pleconaril intranasal spray had reached phase II clinical trial for the treatment of the common cold symptoms and asthma complications. However, the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life. Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure ( valence bond theory) depictions of a single chemical species, whose true structure is best described as the "average" of the idealized, hypot ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
United States Army Research Laboratory
The U.S. Army Combat Capabilities Development Command Army Research Laboratory (DEVCOM ARL) is the U.S. Army's foundational research laboratory. ARL is headquartered at the Adelphi Laboratory Center (ALC) in Adelphi, Maryland. Its largest single site is at Aberdeen Proving Ground, Maryland. Other major ARL locations include Research Triangle Park, North Carolina, White Sands Missile Range, New Mexico, Graces Quarters, Maryland, and NASA's Glenn Research Center, Ohio and Langley Research Center, Virginia. ARL also has regional sites in Playa Vista, California (ARL West), Chicago (ARL Central), Austin, TX (ARL South), and Boston (ARL Northeast). DEVCOM ARL has three directorates: *Army Research Office, located in Research Triangle Park *Army Research Directorate *Research Business Directorate History Before the forming of the ARL, the United States Army had research facilities dating back to 1820 when the laboratory at Watertown Arsenal, Massachusetts, studied pyrote ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of heterocyclic chemistry focuses especially on unsaturated derivatives, and the preponderance of work and applications involves unstrained 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quino ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
