- Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents
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The reactions of thioamides with ortho-nitro-substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex molecules such as peptides or steroids were possible. A mild and efficient method for the synthesis of various iodonium ylides was established. DFT calculations suggested that the halogen bonding between a thioamide and iodonium ylide was important in this chemoselective coupling reaction. The potential use of enaminones conjugated with pharmaceuticals as prodrugs was also demonstrated.
- Saito, Masato,Kobayashi, Yusuke,Takemoto, Yoshiji
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- An expeditious synthesis of cyclic imides
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Trifluoroacetamide was reacted with diacids in the presence of N-ethyl- N-dimethylaminopropylcarbodiimide and of 1-hydroxybenzotriazole to afford cyclic imides of different ring size, providing a single step asymmetric synthesis of thalidomide.
- Flaih, Nazar,Pham-Huy, Chuong,Galons, Herve
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- The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen
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The synthesis of aminoglutethimide via a one-pot coupling of nitrobenzene, ethyl 2-chlorobutyrate and 3-bromopropionitrile has been achieved via a process involving sequential vicarious nucleophilic aromatic substitution and alkylation.
- Bushell, Simon M.,Crump, J. Paul,Lawrence, Nicholas J.,Pineau, Guillaume
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p. 2269 - 2274
(2007/10/03)
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- A mild preparation of 2,6-piperidinediones
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Substituted glutaric acids reacted with alkyloxyamines in the presence of M-ethyl-N-dimethylaminopropylcarbodiimide hydrochloride to form 1-alkyloxy-2,6-piperidinediones. The protecting group on the nitrogen was easily removed in high yield. This process is exemplified by the preparation of aminoglutethimide.
- Zhu, Jiarong,Chuong, Pham Huy,Lemoine, Pascale,Tomas, Alain,Galons, Herve
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p. 1923 - 1926
(2007/10/03)
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- Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents
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A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.
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- Aromatase Inhibitors. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 3-Alkylated 3-(4-Aminophenyl)piperidine-2,6-diones
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The synthesis and biological evaluation of 3-alkyl-substituted 3-(4-aminophenyl)piperidine-2,6-diones as inhibitors of estrogen biosynthesis are described .In vitro compounds 4-14 showed a stronger inhibition of human placental aromatase compared to aminoglutethimide (AG, compound 3), which recently has become used for the treatment of hormone-dependent breast cancer.The most active derivative, compound 10, showed a 93-fold stronger inhibition than AG.With the exception of 5, 7, and 8, all other compounds exhibited similar or decreased inhibition of bovine adrenal desmolase compared to AG.Compounds 4 and 6-12 showed a stronger inhibition of the plasma estradiol concentration of pregnant mare serum gonadotropin (PMSG) primed Sprague-Dawley (SD) rats compared to the parent compound.Compounds 4, 6-8, 10, and 12 inhibited the testosterone-stimulated tumor growth of ovariectomized 9,10-dimethyl-1,2-benzanthracene (DMBA) tumor-bearing SD rats more strongly than AG.Being stronger and more selective inhibitors of the estrogen biosynthesis than AG, some of the newly developed derivatives of AG might be better candidates for the treatment of the hormone-dependent human breast cancer.
- Hartmann, Rolf W.,Batzl, Christine
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p. 1362 - 1369
(2007/10/02)
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