4338-95-8

Usage

Uses

Used in Chemical Synthesis:
METHYL AMINOMETHANIMIDOTHIOATE HYDROIODIDE is used as a reactant for the synthesis of alkyl/acyl guanidines and pyrimidine derivatives. Its ability to form stable intermediates and facilitate reactions makes it a valuable component in the production of these compounds.
Used in Pharmaceutical Industry:
METHYL AMINOMETHANIMIDOTHIOATE HYDROIODIDE is used as a catalyst in the rearrangement of penicillin 1-oxides. This application is crucial in the production of semi-synthetic penicillins, which are widely used as antibiotics to treat various bacterial infections.

InChI:InChI=1/C2H6N2S.HI/c1-5-2(3)4;/h1H3,(H3,3,4);1H

Upstream product

• 17356-08-0 thiourea 
• 74-88-4 methyl iodide 
• 30738-99-9 thiourea 

Downstream Products

• 5441-10-1 (4-amino-phenyl)-guanidine; hydriodide 
• 57-00-1 Creatinine 
• 22059-41-2 S-(3-Guanidino-propyl)-thioschwefelsaeure 
• 22059-36-5 S-<2-(1-Methyl-guanidino)-aethyl>-thioschwefelsaeure 
• 22059-37-6 S-<2-(1-Aethyl-guanidino)-aethyl>-thioschwefelsaeure 
• 22059-38-7 S-<2-(1-Isopropyl-guanidino)-aethyl>-thioschwefelsaeure 
• 22059-42-3 S-(4-Guanidino-butyl)-thioschwefelsaeure 
• 630-10-4 selenourea 
• 46228-36-8 1-(3,4-dichlorobenzyl)guanidine 
• 16175-67-0 2-amino-6,7-dimethoxy-4(1H)-quinazolinone 
• 27622-90-8 2-amino-4-methyl-6-methylthio-1,3,5-triazine 
• 90905-31-0 2-(methylsulfanyl)pyrimidine-5-carbaldehyde 
• 81440-86-0 N-<<5-(1,1-dimethylethyl)-2-hydroxy-3-iodophenyl>methyl>guanidine 
• 126685-80-1 5-Benzoyl-4-methyl-2-methylthiopyrimidine 

Relevant academic research and scientific papers

Synthesis of guanidinopropyl triethoxysilane and its homopolymer as a new class of organosilicon antibacterial agents

In current work guanidinopropyl triethoxysilane was synthesized for the first time. It was shown that this compound is stable as a salt of hydroiodic acid, however, it easily undergoes condensation when heated in water, forming a water-soluble branched homopolymer. Aqueous solutions of guanidinopropyl triethoxysilane and its branched homopolymer showed moderate antibacterial activity against Staphylococcus aureus and Escherichia coli.

Novel potent organoselenium compounds as cytotoxic agents in prostate cancer cells

A series of 17 symmetrical substituted imidothiocarbamate and imidoselenocarbamate derivatives has been synthesized by reacting appropriately substituted acyl chlorides with alkyl imidothiocarbamates and alkyl imidoselenocarbamates. The antitumoral activities of the compounds were evaluated in vitro by examining their cytotoxic effects against human prostate cancer cells (PC-3). Five compounds showed interesting activity levels and 3p (IC50 = 1.85 μM) was 7.3 times more active than the standard etoposide used in the treatment of prostate cancer and emerges as the most interesting compound.

Efficient Catalysts of Acyclic Guanidinium Iodide for the Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides under Mild Conditions

We have studied the synthesis of five-membered cyclic carbonates through the cycloaddition of CO 2 to epoxides by using acyclic guanidinium salts. We have found that the cycloaddition reactions proceed smoothly at ordinary temperatures and pressures and result in good yields when acyclic guanidinium iodides are employed as catalysts. Both cation moiety and anion moiety of the guanidinium salts play important roles in their catalytic activity. It is essential to have active hydrogens on the cation moiety as well as an iodide ion as the anion moiety so as to achieve good catalytic activity. Guanidinium iodides with three or more active hydrogens give cyclic carbonates in high yields in polar solvents such as 1-methylpyrrolidin-2-one, whereas the guanidinium iodides with one or two active hydrogens show good catalytic activity in less polar solvents such as 2-methyltetrahydrofuran.

Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties

Herein we describe the development of an efficient one-pot regioselective synthesis protocol to obtain N-protected or N-deprotected 1,5-diaryl-3-amino-1,2,4-triazoles from N-acyl-N-Boc-carbamidothioates. This improved protocol using microwave irradiation and low reaction times (up to 1 h) furnished desired compounds in yields ranging from 50 to 84%. This chemistry is useful for a variety of aromatic groups with electronically diverse substituents. The design and correct derivation of the amino group led to compounds able to inhibit cholinesterases with good IC50 of up to 1 μM. Also, the mode of action (mixed-type) and SAR analysis for this series of compounds was described by means of kinetic and molecular modelling evaluations, showing potential for this class of compounds as new scaffolds for this biological activity.

Rapid access to novel 2-alkylthiopyrimidine derivatives and attempt of their Tacrine analogs synthesis

A variety of novel 2-alkylthiopyrimidines were synthesized through simple condensation of arylidenemalononitriles with different 2-alkylthiouronium halide derivatives catalyzed by anhydrous potassium carbonate (K2CO3). The reactions have been carried out under mild conditions in i-PrOH, and the products were obtained in moderate to good yields with a simple work-up method. Subsequently, some examples of these compounds have been converted into Tacrine analogs by applying the Friedl?nder reaction.

GUANIDINE DERIVATIVE AND MEDICAL USE THEREOF

A compound has a guanidine skeleton that inhibits the protease activity of MALT1 and exerts a therapeutic or prophylactic effect on autoimmune disease such as psoriasis or allergic disease such as atopic dermatitis. The guanidine derivative is typified by the following formula or a pharmacologically acceptable salt thereof.

Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 μg/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxa-1,3-diazole fluorophores) with good activity (MIC = 0.5 μg/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane.

DIPHENYL PYRAZOLE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

PROBLEM TO BE SOLVED: To provide a compound that functions to inhibit MALT1 protease activity and is useful as an agent for treating or for preventing autoimmune disease such as multiple sclerosis and psoriasis. SOLUTION: The present invention provides a diphenyl pyrazole derivative represented by the following formula or a pharmacologically acceptable salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Synthesis and evaluation of cationic norbornanes as peptidomimetic antibacterial agents

A series of structurally amphiphilic biscationic norbornanes have been synthesised as rigidified, low molecular weight peptidomimetics of cationic antimicrobial peptides. A variety of charged hydrophilic functionalities were attached to the norbornane scaffold including aminium, guanidinium, imidazolium and pyridinium moieties. Additionally, a range of hydrophobic groups of differing sizes were incorporated through an acetal linkage. The compounds were evaluated for antibacterial activity against both Gram-negative and Gram-positive bacteria. Activity was observed across the series; the most potent of which exhibited an MIC's ≤ 1 μg mL-1 against Streptococcus pneumoniae, Enterococcus faecalis and several strains of Staphylococcus aureus, including multi-resistant methicillin resistant (mMRSA), glycopeptide-intermediate (GISA) and vancomycin-intermediate (VISA) S. aureus.

Convenient synthesis of acyclic guanidines from isothiouronium iodides and amines without protection of the amino groups

Acyclic guanidines were obtained in one step by reaction of isothiouronium iodides with an equimolar amount of various amines in tetrahydrofuran. The reactions proceeded under ambient conditions without N-protection/deprotection to afford the corresponding substituted guanidines in quantitative yields. Georg Thieme Verlag Stuttgart New York.