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ECHA InfoCard | 100.054.745 |
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Formula | C13H15BrN4O2 |
Molar mass | 339.193 g·mol−1 |
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Melting point | 225 to 228 °C (437 to 442 °F) |
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Brodimoprim is a structural derivative of trimethoprim. In brodimoprim, the 4-methoxy group of trimethoprim is replaced with a bromine atom.
As trimethoprim, brodimoprim is a selective inhibitor of bacterial dihydrofolate reductase. [1]
The treatment of Dimethyl 2,6-dimethoxybenzene-1,4-dicarboxylate [16849-68-6] (1) with hydroxylamine in PPA gives the hydroxamide, PC12398304 (2). Further treatment with PPA led to methyl 4-amino-3,5-dimethoxybenzoate [56066-25-2] (3). Sandmeyer reaction led to Methyl 4-bromo-3,5-dimethoxybenzoate [26050-64-6] (4). Saponification of the ester formed 4-Bromo-3,5-dimethoxybenzoic acid [56518-42-4] (5). Halogenation with thionyl chloride gave 4-Bromo-3,5-dimethoxybenzoyl chloride [56518-43-5] (6). Rosenmund reduction gave 4-Bromo-3,5-dimethoxybenzaldehyde [31558-40-4] (7). {Alternatively DIBAL meant that FGI from ester to aldehyde was accomplished in only 1 step}. Knoevenagel condensation with 3-Methoxypropionitrile [110-67-8] (8) afforded [56518-39-9] (9). Finally, condensation with Guanidine [113-00-8] completed the synthesis of Brodimoprim (10).
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.
In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.
Acyloin condensation is a reductive coupling of two carboxylic esters using impure metallic sodium to yield an α-hydroxyketone, also known as an acyloin.
The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group α to a carbonyl group (2).
The Nicolaou Taxol total synthesis, published by K. C. Nicolaou and his group in 1994 concerns the total synthesis of taxol. Taxol is an important drug in the treatment of cancer but also expensive because the compound is harvested from a scarce resource, namely the pacific yew.
Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.
Etonitazene, also known as EA-4941 or CS-4640, is a benzimidazole opioid, first reported in 1957, that has been shown to have approximately 1,000 to 1,500 times the potency of morphine in animals.
Latamoxef is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.
Atiprimod is a substance being studied in the treatment of certain multiple myelomas and other advanced cancers. It may block the growth of tumors and the growth of blood vessels from surrounding tissue to the tumor. This drug is also being researched as a potential treatment for various autoimmune diseases.
Efaroxan is an α2-adrenergic receptor antagonist and antagonist of the imidazoline receptor.
Strychnine total synthesis in chemistry describes the total synthesis of the complex biomolecule strychnine. The first reported method by the group of Robert Burns Woodward in 1954 is considered a classic in this research field.
Proxorphan (INN), also known as proxorphan tartate (USAN), is an opioid analgesic and antitussive drug of the morphinan family that was never marketed. It acts preferentially as a κ-opioid receptor partial agonist and to a lesser extent as a μ-opioid receptor partial agonist.
Cholesterol total synthesis in chemistry describes the total synthesis of the complex biomolecule cholesterol and is considered a great scientific achievement. The research group of Robert Robinson with John Cornforth published their synthesis in 1951 and that of Robert Burns Woodward with Franz Sondheimer in 1952. Both groups competed for the first publication since 1950 with Robinson having started in 1932 and Woodward in 1949. According to historian Greg Mulheirn the Robinson effort was hampered by his micromanagement style of leadership and the Woodward effort was greatly facilitated by his good relationships with chemical industry. Around 1949 steroids like cortisone were produced from natural resources but expensive. Chemical companies Merck & Co. and Monsanto saw commercial opportunities for steroid synthesis and not only funded Woodward but also provided him with large quantities of certain chemical intermediates from pilot plants. Hard work also helped the Woodward effort: one of the intermediate compounds was named Christmasterone as it was synthesized on Christmas Day 1950 by Sondheimer.
Rosefuran (3-methyl-2-prenylfuran) is an organic compound, classified as a terpenoid. It is a minor constituent of the aroma of the rose. Rosefuran is a 2,3-disubstituted furan. It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil. Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.
Borinic acid, also known as boronous acid, is an oxyacid of boron with formula H
2BOH. Borinate is the associated anion of borinic acid with formula H
2BO−
; however, being a Lewis acid, the form in basic solution is H
2B(OH)−
2.
BOMT, also known by its developmental code name Ro 7-2340 and as 6α-bromo-4-oxa-17α-methyl-5α-dihydrotestosterone, is a synthetic steroidal antiandrogen which was first produced in 1970 and was never marketed for medical use. It is the 6α-brominated, 4-oxygenated, and 17α-methylated derivative of the androgen dihydrotestosterone (DHT). Along with benorterone, cyproterone, and flutamide, BOMT was among the earliest antiandrogens to be developed and extensively studied, although it is less well-documented in comparison to the others. BOMT has been investigated clinically in the treatment of benign prostatic hyperplasia, though development for this use did not continue. There was also interest in BOMT for the potential applications of acne, pattern hair loss, and possibly prostate cancer, but it was not developed for these indications either.
1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5H
10O
5 or (–CHOH–)
5, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.