13398-11-3

Upstream product

• 50-00-0 formaldehyd 
• 507-02-8 acetyl iodide 
• 625-56-9 Chloromethyl acetate 
• 110-88-3 1,3,5-Trioxan 
• 75-36-5 acetyl chloride 

Downstream Products

• 157977-99-6 C₁₃H₁₅O₉P 
• 157978-01-3 bis(acetoxymethyl) <(2,4-dichlorophenoxy)carbonyl>phosphonate 
• 773133-82-7 6-(acetyloxymethyl)-9-benzylpurine 
• 629604-05-3 6-(hydroxymethyl)-9-benzylpurine 
• 773133-85-0 6-(hydroxymethyl)-9-(2-deoxy-3,5-di-O-(p-toluolyl)-β-D-erythro-pentofuranosyl)purine 
• 773133-86-1 6-(acetyloxymethyl)-9-(2-deoxy-3,5-di-O-(p-toluolyl)-β-D-erythro-pentofuranosyl)purine 
• 105275-69-2 Acetoxymethyl 5R,3-(4-carbamoylphenoxy)-6S-(1R-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate 
• 1015763-46-8 C₁₇H₂₄O₄ 
• 57721-81-0 3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol acetate 
• 1456545-45-1 4-{[(2R,3S,4R,5S)-4-(4-chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoic acid acetoxymethyl ester 
• 35279-25-5 acetoxymethyl phenyl ether 
• 122-79-2 Phenyl acetate 
• 2623-33-8 4-acetoxyacetanilide 
• 865434-71-5 6-(acetyloxymethyl)-9-(2,3,5-tri-O-(p-toluolyl)-β-D-ribofuranosyl)purine 

Relevant academic research and scientific papers

Synthesis of iodoalkylacylates and their use in the preparation of S-alkyl phosphorothiolates

Synthesis of iodoalkylacylates 3a-f and use of 3c in the preparation of an oligonucleoside phosphorothiate prodrug analog 5 is described.

New monofunctionalized fluorescein derivatives for the efficient high-throughput screening of lipases and esterases in aqueous media

Monoalkylation or acylation of fluorescein (1) with various acyloxymethyl or acyl halides afforded, respectively, a series of ether- (2) and ester-functionalized (3) fluorogenic probes. The highly reactive and water-soluble substrates release fluorescein

Effect of aminomethyl (N-Mannich base) derivatization on the ability of S6-acetyloxymethyl-6-mercaptopurine prodrug to deliver 6-mercaptopurine through hairless mouse skin

A series of 9-aminomethyl-S6-acetyloxymethyl-6-mercaptopurine (9-AM-6-AOM-6-MP) prodrugs have been synthesized and characterized, and their ability to deliver total 6-mercaptopurine (6-MP) through hairless mouse skin has been measured. The 9-AM-6-AOM-6-MP prodrugs are much more soluble in isopropyl myristate (IPM) than S6-acetyloxymethyl-6-MP (6-AOM-6-MP) itself or the corresponding 7-aminomethyl-6-MP (7-AM-6-MP) prodrugs. The 9-AM-6-AOM-6-MP prodrugs were all more effective (1.8-4 times) than 6-AOM-6-MP at delivering total 6-MP, except for the piperidylmethyl derivative which only gave a comparable rate of delivery. The 9-AM-6-AOM-6-MP prodrugs were also more effective (7-27 times) than the corresponding 7-AM-6-MP prodrugs at delivering 6-MP, except for the diethylaminomethyl derivative which only gave a comparable rate of delivery. In contrast to the 9-aminomethyl-S6-pivaloyloxymethyl-6-MP (9-AM-6-POM-6-MP) derivatives which generally delivered as much or more intact S6-pivaloyloxymethyl-6-MP (6-POM-6-MP) as 6-MP, the 9-AM-6-AOM-6-MP derivatives delivered mainly (80-95%) 6-MP from IPM. There was a direct correlation between log experimental permeability coefficients for delivery of total 6-MP (P(Σ)) and the calculated solubility parameter values for the 9-AM-6-AOM-6-MP prodrugs (δ(j)), with the P(Σ) generally decreasing as the value of δ(j) approached that of the vehicle, IPM. There was no significant effect of the prodrugs:IPM suspensions on the skin compared with 6-MP:IPM suspension or IPM, as determined by a second application of a standard solute:vehicle complex.

Synthesis and biological evaluation of 1,4-dihydropyridine calcium channel modulators having a diazen-1-ium-1,2-diolate nitric oxide donor moiety for the potential treatment of congestive heart failure

A group of racemic 4-aryl(heteroaryl)-1,4-dihydro-2,6-dimethyl-3- nitropyridines possessing nitric oxide donor O2-acetoxymethyl-1-(N- ethyl-N-methylamino, or 4-ethylpiperazin-1-yl)diazen-1-ium-1,2-diolate, C-5 ester substituents were synthesized by coupling the respective 4-aryl(heteroaryl)-1,4-dihydro-2,6-dimethyl-3-nitropyridine-5-carboxylic acids with either O2-acetoxymethyl-1-[N-(2-methylsulfonyloxyethyl)-N- methylamino]diazen-1-ium-1,2-diolate, or O2-acetoxymethyl-1-[4-(2- methylsulfonyloxyethyl)piperazin-1-yl]diazen-1-ium-1,2-diolate. Compounds having a C-4 2-pyridyl, 4-pyridyl, 2-trifluoromethylphenyl, or benzofurazan-4-yl substituent exhibited more potent smooth muscle calcium channel antagonist activity (IC50's in the 0.37-1.09μM range) than related analogs having a C-4 3-pyridyl substituent (IC50's=3.03-9.14μM range) relative to the reference drug nifedipine (IC50=9.13nM). The point of attachment of C-4 isomeric pyridyl substituents was a determinant of smooth muscle calcium channel antagonist activity where the relative potency profile was 4-pyridyl>2-pyridyl>3-pyridyl. Replacement of the C-5 methyl ester substituent of methyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2- trifluoromethylphenyl)pyridine-5-carboxylate (Bay K 8644) by an O 2-acetoxymethyl-1-(N-ethyl-N-methylamino)diazen-1-ium-1,2-diolate, or O2-acetoxymethyl-1-(4-ethylpiperazin-1-yl)diazen-1-ium-1,2-diolate, C-5 ester substituent provided compounds, which exhibited a lower, yet respectable, cardiac positive inotropic effect (IC50's=4.82 and 4.05μM, respectively) relative to the reference drug Bay K 8644 (IC 50=0.30μM). All compounds released nitric oxide upon incubation with either phosphate buffer at pH7, or porcine liver esterase. However, the percentage nitric oxide released was up to 3-fold higher (76%) when these O 2-acetoxymethyl-1-(alkylamino)diazen-1-ium-1,2-diolates were incubated with guinea pig serum. These results suggest that ·NO would be released in vivo, upon cleavage by nonspecific serum esterases, preferentially in the vascular endothelium where it may enhance smooth muscle calcium channel antagonist activity.

PRODRUGS OF 4-((1R,3S)-6-CHLORO-3-PHENYL-2,3-DIHYDRO-1H-INDEN-1-YL)-1,2,2-TRIMETHYLPIPERAZINE AND 4-((1/R,3S)-6-CHLORO-3-(PHENYL-D5)-2,3-DIHYDRO-1H-INDEN-1-YL)-2,2-DIMETHY-1-(METHYL-D3)PIPERAZINE

The present invention relates to prodrugs of 4-((1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl)- 1,2,2-trimethylpiperazine in the form of 1a and 1b; and 4-((1R,3S)-6-chloro-3-(phenyl-d5)-2,3-dihydro- 1H-inden-1-yl)-2,2-dimethyl-1-(methyl-d

Prodrugs of NH-acidic compounds

The invention provides a method of sustained delivery of a lactam, imide, amide, sulfonamide, carbamate or urea containing parent drug by administering to a patient an effective amount of a prodrug compound of the invention wherein upon administration to the patient, release of the parent drug from the prodrug is sustained release. Prodrug compounds suitable for use in the methods of the invention are labile conjugates of parent drugs that are derivatized through carbonyl linked prodrug moieties. The prodrug compounds of the invention can be used to treat any condition for which the lactam, imide, amide, sulfonamide, carbamate or urea containing parent drug is useful as a treatment.

SUBSTITUTED PYRROLIDINE-2-CARBOXAMIDES

There are provided compounds of the formula wherein X, Y, Z, R1, R2, R3 and R4 are as described herein and enantiomers and pharmaceutically acceptable salts and esters thereof. The compounds are useful as anticancer agents.

Reaction of α-(n-alkylcarbonyloxy)alkyl (ACOA) halides with 4-hydroxyacetanilide and 2,2,5,7,8-pentamethyl-6-chromanol: The effect of steric hindrance on reaction path

A convenient synthesis of α-(n-alkylcarbonyloxy)alkyl (ACOA) iodides has been developed and a homologous series of n-alkylcarbonyloxymethyl (ACOM) iodides have been used to alkylate 4-hydroxyacetanilide (acetaminophen, APAP), a sterically unhindered phenol, and a sterically hindered phenol (2,2,5,7,8-pentamethyl-6-chromanol). Steric hindrance was not a significant factor in the ratio of acylated (Path b) to alkylated (Path a) for these reactions. Given the reported toxicity associated with sterically hindered ACOM prodrugs, n-alkyl ACOM and ACOA promoieties present themselves as viable alternatives to the more commonly used pivalate-based derivatives. Georg Thieme Verlag Stuttgart.

Reaction of alkylcarbonyloxymethyl halides with phenols: reevaluating the influence of steric hindrance

Evidence is presented that contradicts an earlier finding that, in the absence of steric hindrance, the coupling reaction of alkylcarbonyloxymethyl (ACOM) halides with phenols favors acylated product. A one-step synthesis is used to generate sterically unhindered ACOM iodides, which are then reacted with several phenols to give mainly alkylated phenol.

Carbapenem derivatives

Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti-microbial activities against β-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position on the carbapenem ring thereof: