- Stereoselective Grignard additions to N-formyl hydrazone: A concise synthesis of NoxafilR side chain and a synthesis of Noxafil R
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Addition of ethyl Grignard reagent to the formyl hydrazone 11 via in situ silylation provided the corresponding formyl hydrazine with excellent diastereoselectivity in favor of the desired S,S-diastereoisomer 6. Treatment of 6 with the phenyl carbamate 13 efficiently provided the O-benzyl protected Noxafil, which was deprotected to provide NoxafilR.
- Saksena, Anil K.,Girijavallabhan, Viyyoor M.,Wang, Haiyan,Lovey, Raymond G.,Guenter, Frank,Mergelsberg, Ingrid,Puar, Mohinder S.
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- Synthesis, Crystal Structure, Anti-Bone Cancer Activity and Molecular Docking Investigations of the Heterocyclic Compound 1-((2S,3S)-2-(Benzyloxy)Pentan-3-yl) -4-(4-(4-(4-Hydroxyphenyl)Piperazin-1-yl) Phenyl)-1H-1,2,4-Triazol-5(4H)-One
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Heterocyclic compound 1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-1H-1,2,4-triazol-5(4H)-one (1) designed using 4-(4-(4-aminophenyl)piperazin-1-yl)phenol (2) and (S)-N′-(2-(benzyloxy)propylidene)formohydrazide (3) as start materials is successfully obtained via a multistep synthesis and finally characterized by IR, 1H NMR, and single crystal X-ray diffraction. In addition, the in vitro anticancer activities of newly synthesized compound 1 are evaluated against three human bone cancer cell lines U2OS, Saos-2, and GC9811. In addition, the molecular docking is used to study the potential antiviral activity of 1 by calculating the binding sites for the 1AS0 protein.
- Lv,Zhang,Wang,Pan,Liu
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- Method for synthesizing N'-[(2S, 3S)-2-(benzyloxy) pentyl-3-base] formylhydrazine
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A method for synthesizing N'-[(2S, 3S)-2-(benzyloxy) pentyl-3-base] formylhydrazine comprises the following steps: reacting (S)-2-benzyloxypropionic acid with an acylation reagent to obtain (S)-2-benzyloxy propionyl chloride; adding a palladium barium sulfate catalyst into o-xylene and reacting in hydrogen atmosphere for 15-30 min; adding (S)-2-benzyloxy propionyl chloride hydrogen atmosphere forreflux reaction until hydrogen is not absorbed; after the reaction is finished, the catalyst is filtered and the o-xylene is removed to obtain (S)-2-benzyloxypropionaldehyde; reacting the (S)-2-benzyloxypropionaldehyde with formylhydrazine, removing the solvent after finishing the reaction, and post-treating to obtain (S)-N'-(2 benzyloxypropyl) formylhydrazine; reacting the (S)-N'-(2 benzyloxypropyl) formylhydrazine with a Grignard reagent, and post-treating to obtain N'-((2s,3s)- 2-(benzyloxy) pentyl-3-base] formylhydrazine. According to the invention, an acylating reagent which is low in price and safer and more environment-friendly in reaction and a palladium barium sulfate catalyst which can be recycled for a plurality of times are used as reaction raw materials, so that the reaction process more conforms to the principle of atom economy, and the reaction is milder.
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- A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE
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The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.
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- Method for synthesizing N'-[(2S,3S)-2-(benzyloxy) penta-3-yl]formhydrazide
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The invention discloses a method for synthesizing N'-[(2S,3S)-2-(benzyloxy) penta-3-yl]formhydrazide, comprising the following steps: letting (S)-2-benzyloxy propionic acid react with ethene diamine to obtain (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole; adding metallic sodium into (S)-2-(1-benzyloxyethyl)-4,5-dihydro-1H-imidazole under the protection of nitrogen, stirring and reacting and processing to obtain (S)-2-benzyloxy propionaldehyde; letting (S)-2-benzyloxy propionaldehyde react with formhydrazide and carrying out post-treatment to obtain (S)-N'-(2-benzyloxy propylidene)formhydrazide; letting (S)-N'-(2-benzyloxy propylidene)formhydrazide react with a Grignard reagent and carrying out post-treatment after the reaction so as to obtain the product N'-[(2S,3S)-2-(benzyloxy)penta-3-yl]formhydrazide. The method of the invention has the following advantages: no expensive and unsafe organo-aluminum compound is used; preparation cost is low; post-treatments are simple; and operation is simple.
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- Preparation method of antifungal medicine intermediate
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The invention discloses a preparation method of an antifungal medicine intermediate. The method comprises the following steps: carrying out a condensation reaction on a compound (A) used as a raw material and formylhydrazine in an organic solvent; and purifying the obtained condensation reaction product to prepare the 2-[2S-1-ethyl-2-benzyloxypropylidene]hydrazinecarboxaldehyde (B) intermediate. The preparation method has the advantages of mild reaction conditions, facilitation of step shortening, reduction of the material consumption, reduction of wastes, reduction of the production cost, and facilitation of industrial production.
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Paragraph 0038; 0039
(2017/07/19)
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- Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof
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A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)
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Paragraph 0339
(2014/12/09)
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