34840-23-8

Usage

Uses

1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudourea is used as an intermediate in the synthesis of various compounds for different purposes. The expression is: 1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudourea is used as [application type] for [application reason]
Used in Pharmaceutical Synthesis:
1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudourea is used as a key intermediate in the synthesis of pharmaceutical compounds, such as:
1. Methyl (6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)carbamate: 1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudoeura is synthesized for its potential applications in the development of new drugs targeting various diseases.
2. 2-amino-5-benzyl-6-methyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one: This molecule is synthesized for its potential use in the creation of novel therapeutic agents.
3. Methyl-5-[(3-hydroxypropyl)thio]-1H-benzo[d]imidazol-2-ylcarbamate (hydroxyalbendazole): 1,3-Bis(methoxycarbonyl)-2-methyl-2-thiopseudoeura is synthesized for its potential applications in the treatment of parasitic infections.
4. Methyl-5-[(4-hydroxyphenyl)thio]-1H-benzo[d]imidazol-2-yl carbamate (hydroxyfenbendazole): This molecule is synthesized for its potential use in the development of new anthelmintic drugs.

InChI:InChI=1/C6H10N2O4S/c1-11-5(9)7-4(13-3)8-6(10)12-2/h1-3H3,(H,7,8,9,10)

Upstream product

• 867-44-7 methyl carbamimidothioate bis(sulfate) 
• 79-22-1 methyl chloroformate 
• 14527-26-5 2-methylisothiourea sulphate 
• 2986-19-8 carbamimidothioic acid methyl ester 
• 17356-08-0 thiourea 
• 77-78-1 dimethyl sulfate 
• 867-44-7 S-Methylisothiourea sulfate 

Downstream Products

• 39259-27-3 N-(p-chlorophenyl)-N',N-dicarbomethoxyguanidine 
• 59759-25-0 N-(p-methoxyphenyl)-N',N-dicarbomethoxyguanidine 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 59759-24-9 N-benzyl-N',N-dicarbomethoxyguanidine 
• 65003-40-9 Methyl 5⁽⁶⁾-carboxybenzimidazole-2-carbamate 
• 87223-53-8 C₁₃H₁₅ClN₄O₅ 
• 95772-68-2 2-carbomethoxyamino-1-methyl-1,4,5,6-tetrahydropyrimidine 
• 105168-86-3 C₁₉H₂₄N₄O₈ 
• 105169-17-3 C₂₀H₂₁N₅O₇S 
• 105169-23-1 C₂₁H₂₃N₅O₇S 
• 105169-22-0 C₂₁H₂₃N₅O₇S 
• 105169-24-2 C₂₂H₂₅N₅O₇S 
• 105169-19-5 C₂₁H₂₃N₅O₇S 
• 105169-18-4 C₂₁H₂₃N₅O₇S 

Relevant academic research and scientific papers

PYRAZOLE-OXAZOLIDINONE COMPOUND FOR ANTI-HEPATITIS B VIRUS

The present invention discloses a pyrazole-oxazolidinone compound having anti-hepatitis B virus activity, which has the structure of formula (I), wherein each variable is as defined herein.

Palauchlor: A practical and reactive chlorinating reagent

Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palauchlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.

Process for the preparation of 9-deazaguanine derivatives

Derivatives of 9-deazaguanine are prepared by reacting an aldehyde or ketone with a dialkylaminomalonate to form the corresponding enamine. The enamine is then reacted with a base to form a cyclic pyrrole. The cyclic pyrrole is reacted with an urea compound or a derivative of carbamimidoic acid to provide a protected guanidino compound. The guanidino is converted to the desired 9-deazaguanine derivative by reacting with trifluoracetic acid or with an alkoxide or hydroxide followed by neutralization with an acid.

Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid

Several heterocycles, such as benzimidazoles, quinoxalines and indoles incorporated into a hydrophenanthrene and naphthalene skeleton, were synthesised from two useful ortho-bromonitro precursors derived from dehydroabietic acid: methyl 12-bromo-13-nitro-deisopropyldehydroabietate and methyl 12-bromo-13,14-dinitro-deisopropyldehydroabietate. The new heterocycles were evaluated for their activity in vitro against several RNA and DNA viruses.

Process for the preparation of 9-deazaguanine derivatives

Derivatives of 9-deazaguanine are prepared by reacting an aldehyde or ketone with a dialkylaminomalonate to form the corresponding enamine. The enamine is then reacted with a base to form a cyclic pyrrole. The cyclic pyrrole is reacted with an urea compound to provide a protected guanidino compound. The guanidino is converted to the desired 9-deazaguanine derivative by reacting with trifluoracetic acid or with an alkoxide or hydroxide followed by neutralization with an acid.

2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity

Polysubstituted o-phenylenediamines were synthesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio- and 2-trifluoro-methylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 11-(pyridin-2-ylthio)dibenzo[a,c]phenazine were synthesized too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.

Synthesis, Tubulin Binding, Antineoplastic Evalutaion, and Structure-Activity Relationship of Oncodazole Analogues

n an attempt to identify a soluble oncodazole analogue that could be easily formulated, a series of substituted oncodazoles was synthesized and evaluated for tubulin binding affinity, in vitro cyctotoxicity against cultured mouse B-16 cells, and ability to prolong lifespan at the maximally tolerated dose in the P388 mouse leukemia model.Biological evaluation of all the isomeric methyloncodazoles demonstrated the thiophene 4'-position to be the only site of significant bulk tolerance, although substitution of this position with polar or charged functional groups abolished biological activity.Simple esters of the 4'-carboxymethyloncodazole were shown to have enhanched antitumor activity and tubulin binding affinity relative to oncodazole.Despite a failure of this study to identify a water-soluble oncodazole with antitumor activity, the structure-activity relationship developed led to a derivative with enhanced activity in the P388 leukemia model and facilitated the preparation of a biologically active photolabile analogue.

Synthesis and central nervous system properties of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines

A series of 2-[(alkoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines was prepared and evaluated for central nervous system (CNS) effects (antidepressant, anticonvulsant, muscle relaxant, and depressant) in animal models. Some separation of those CNS activities was achieved through substitutions on the phenyl and imidazoline moieties. Halo-substituted phenyl compounds were among the most potent antidepressants in this series, while imidazole N-alkylation produced compounds with increased depressant effects (loss of righting reflex, mouse behavior). Comparison of in vitro and in vivo data for pairs of 2-[(methoxycarbonyl)amino]-4(5)-phenyl-2-imidazolines and their parent, 2-amino-4(5)-phenyl-2-imidazolines, suggests that the title compounds were prodrugs for the 2-amino-4(5)-phenyl-2-imidazolines in inhibition of norepinephrine reuptake.

Substituted phenylguanindines and method

Phenylguanidine derivatives are provided having the structure STR1 wherein R is hydrogen, lower alkyl, cycloalkyl, lower alkoxy, phenyl, phenylalkyl, phenoxy, phenylalkoxy, lower alkoxyalkyl, phenoxyalkyl, alkylamino, dialkylaminoalkyl, alkylthio, phenylthio, phenylthioalkyl, and alkylthioalkyl; R1 is lower alkyl or benzyl; R2 is hydrogen, lower alkoxy carbonyl, and lower alkanoyl; R3 is lower alkyl, cycloalkylalkyl, lower alkenyl, lower alkynyl or benzyl; and n is 0 or 1. These compounds are useful as anthelmintic agents.

Substituted phenylguanidines and method

Phenylguanidine derivatives are provided having the structure STR1 wherein R is lower alkyl, cycloalkyl, cycloalkylalkyl, lower alkenyl, lower alkynyl, phenyl or benzyl; R1 and R2 may be the same or different and are lower alkyl or R1 and R2 may be taken together to form an alkylene linking group of 2 or 3 carbons or an o-phenylene group; R3 and R4 are the same or different and are lower alkyl, benzyl or phenyl; and n is 0 or 1. These compounds are useful as anthelmintic agents.