98.0%| A1455520|Formula:C8H8N2OS|Molecular Weight:180.226950000+ products instock " />
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents
Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina , et al. J. Enzym. Inhib. Med. Ch.,2022,37(1):2725-2741. DOI: 10.1080/14756366.2022.2127701 PubMed ID: 36189734
More
Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.
Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition
Purchased from AmBeed: 934-32-7 ; 1477-42-5 ; 5464-79-9 ; 5464-79-9 ; 136-95-8 ; 95-24-9 ; 533-30-2 ; 1123-93-9 ; 6285-57-0 ; 15864-32-1 ; 29927-08-0 ; 348-40-3 ; 58-63-9 ; 4570-41-6 ; 75985-45-4 ; 24280-93-1 ; 2536-91-6 ; 19952-47-7 ; 1747-60-0 ; 777-12-8 ; 58-63-9 ; 63837-12-7 ...More
CAS No. : | 1747-60-0 | MDL No. : | MFCD00005787 |
Formula : | C8H8N2OS | Boiling Point : | - |
Linear Structure Formula : | C7H3(OCH3)NSNH2 | InChI Key : | KZHGPDSVHSDCMX-UHFFFAOYSA-N |
M.W : | 180.23 | Pubchem ID : | 15630 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; bromine; chlorine; In water; 1,2-dichloro-ethane; | EXAMPLE 1 182 parts of p-methoxyphenyl-thiourea are suspended in 2,200 parts of ethylene chloride. To dehydrate the mixture, 200 parts of the solvent are distilled off under atmospheric pressure. The suspension is cooled to 30 C. and 6 parts of bromine are added. 71 parts of chlorine gas are then passed in over 4 hours at the same temperature, whilst cooling the mixture slightly, and the batch is then refluxed for 1 hour. Thereafter it is allowed to cool to about 70 C. and 1,000 parts of water are hereupon added, causing the solid to dissolve. After removing the organic phase, the ethylene chloride emulsified in the aqueous phase is stripped off in steam. The clear solution is then rendered alkaline, at 50 C., with 130 parts of concentrated ammonia. After the mixture has cooled to room temperature, the precipitate is filtered off, washed neutral with water and dried. The yield is 171 parts of 6-methoxy-2-aminobenzothiazole of melting point 163-165 C., corresponding to 95% of theory. | |
With bromine; acetic acid; at 0 - 15℃; for 2h; | General procedure: One of compounds 6a-6d (10 mmol) and ammonium thiocyanate (0.91 g, 12 mmol) were dissolved in glacial acetic acid and the reaction mixture was stirred for 4 h. Bromine (0.6 mL, 11 mmol) in glacial acetic acid (8 mL) was added dropwise to the reaction mixture and it was stirred at 15C for 2 h. Then, the solid was filtered off and dissolved in hot water. The filtrate was quenched with saturated aqueous sodium bicarbonate. The solid residue of the corresponding product 8a-8d was filtered off. | |
With bromine; In dichloromethane; at 5℃; | General procedure: Substituted phenylthiourea (0.1 mol) was taken in CHCl3 and stirred with a mechanical stirrer and bromine (0.1 mol) was added drop by drop for a period of an hour with continuous stirring. The temperature was maintained <5C. After bromine addition, the stirring was maintained for 4-5 hours. The product obtained was dried, followed by SO2 water treatment and filtered. The filtrate obtained was treated with aq. NH3 in neutral conditions. The obtained precipitate was filtered, dried, and recrystallized from absolute alcohol. |