- Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin
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High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.
- Abdelkafi, Hajer,Michau, Aurélien,Pons, Valérie,Ngadjeua, Flora,Clerget, Alexandra,Ait Ouarab, Lilia,Buisson, David-Alexandre,Montoir, David,Caramelle, Lucie,Gillet, Daniel,Barbier, Julien,Cintrat, Jean-Christophe
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p. 8114 - 8133
(2020/09/21)
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- Preparation method of lorazepam intermediate
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The invention provides a preparation method of a lorazepam intermediate, the lorazepam intermediate is 7-chloro-5-(2-chlorphenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one-4-oxide, and the preparationmethod comprises the following steps: (1) carrying out acylation reaction on 2-amino-2', 5-dichlorobenzophenone and chloroacetyl chloride to prepare 2-chloroacetamido-2', 5-dichlorobenzophenone, (2) reacting 2-chloroacetamido-2', 5-dichlorobenzophenone with urotropine and ammonium acetate to prepare 7-chloro-5-(2-chlorphenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one, and (3) carrying out a reaction on the 7-chloro-5-(2-chlorphenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one and ammonium acetate to obtain 7-chloro-5-(2-chlorphenyl)-1, 3-dihydro-2H-1, 4-benzodiazepin-2-one-4-oxide. The preparationmethod disclosed by the invention is simple and convenient, mild in reaction condition, high in yield, good in product quality and low in cost.
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Paragraph 0072-0075; 0084-0087
(2020/12/15)
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- Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives
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A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).
- Cheng, Pi,Zhang, Quan,Ma, Yun-Bao,Jiang, Zhi-Yong,Zhang, Xue-Mei,Zhang, Feng-Xue,Chen, Ji-Jun
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supporting information; scheme or table
p. 3787 - 3789
(2009/04/06)
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- Efficient synthesis of 3-hydroxy-1,4-benzodiazepines oxazepam and lorazepam by new acetoxylation reaction of 3-position of 1,4-benzodiazepine ring
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Simple, efficient, and scalable syntheses of 3-hydroxy-1,4-benzodiazepines, oxazepam (1), and lorazepam (2) were developed. The syntheses are based on the new acetoxylation reaction of the 3-position of the 1,4-benzodiazepine ring. The reaction involves iodine (20-50 mol %)-catalyzed acetoxylation in the presence of potassium acetate (2 equiv) and potassium peroxydisulfate (1-2 equiv) as a stoichiontetric oxidant affording the corresponding 3-acetoxy-1,4- benzodiazepines in good-to-high yields. The latter were converted by selective saponification to 3-hydroxy-1,4-benzodiazepines of very high purity (>99.8%) in an overall yield of 83% (oxazepam) and 64% (lorazepam).
- Cepanec, Ivica,Litvic, Mladen,Pogorelic, Ivan
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p. 1192 - 1198
(2012/12/23)
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- Synthesis and spectral properties of 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines
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A series of twelve new 2-[(o- and p-substituted)aminophenyl]-3H-5-[(o- and p-substituted)phenyl]-7-chloro-1,4-benzodiazepines, which have possible pharmacological properties has been obtained. The synthesis was carried out following six steps. The structure of all products was corroborated by ir, 1H nmr, 13C nmr and ms. In addition for the compound 2-(o-chloroaminophenyl)-3H-5-(o-fluorophenyl)-7-chloro-1,4-benzodiazepine 7, its structure was confirmed by X-ray diffraction.
- Cortes Cortes,Salazar Franco,Garcia Mellado
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p. 663 - 669
(2007/10/03)
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- Process for preparing a 7-chloro-5-(2-chlorophenyl)-benzodiazepinone
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A process for preparing 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one of the formula: STR1 utilizing 2',5-dichloro-2-aminobenzophenone, phthalimidoglycine and hydrazine in a single passage and in a single reaction medium under critical reaction conditions.
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- Process for preparing benzodiazepines
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1,4-Benzodiazepin-2-ones are prepared via the reaction of a haloacetamidophenyl ketone with hexamethylenetetramine in the presence of ammonia. The 1,4-benzodiazepin-2-ones so prepared are known compounds useful as muscle relaxant and anti-convulsant agents.
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