20069-28-7

Basic information

• Product Name: (PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID
• Synonyms: 2-(pyrrolidine-1-carbothioylsulfanyl)acetate
• CAS NO: 20069-28-7
• Molecular Formula: C₇H₁₁NO₂S₂
• Molecular Weight: 205.301
• Mol File: 20069-28-7.mol

Chemical Properties

• Boiling Point: 353.6°C at 760 mmHg
• Flash Point: 167.6°C
• Appearance: /
• Density: 1.425g/cm³
• Vapor Pressure: 5.99E-06mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: (PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID(20069-28-7)
• EPA Substance Registry System: (PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID(20069-28-7)

Safety Data

• Hazardous Substances Data: 20069-28-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID is used as a building block or intermediate in organic synthesis for its unique structural features, which can be leveraged to create novel compounds with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID may serve as a precursor or a key component in the development of new drugs, potentially targeting a range of therapeutic areas due to its distinctive chemical characteristics.
Used in Material Science:
(PYRROLIDIN-1-YLCARBONOTHIOYL)THIO]ACETIC ACID could be utilized in material science for the development of new materials with unique properties, such as improved reactivity, stability, or specific interactions with other molecules, owing to its sulfur-containing thio group.

InChI:InChI=1/C7H11NO2S2/c9-6(10)5-12-7(11)8-3-1-2-4-8/h1-5H2,(H,9,10)

Upstream product

• 123-75-1 pyrrolidine 
• 75-15-0 carbon disulfide 
• 3926-62-3 sodium monochloroacetic acid 
• 109-01-3 1-methyl-piperazine 
• 79-11-8 chloroacetic acid 

Downstream Products

• 135327-48-9 tri-cyclohexyltin pyrrolinyldithiocarbamate 

Relevant articles and documents

Ensembling three multicomponent reactions for the synthesis of a novel category of pseudo-peptides containing dithiocarbamate and N,X-heterocylic groups

Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS2 and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S, O), ketone and ammonia. The final MCR is Ugi reaction to afford the corresponding three-dimensional pseudo-peptides. Various Asinger imines, carboxylic acids and isocyanides were applied in this protocol to provide diversities of pseudo-peptides in high to excellent yields.

Synthesis, characterization and biological evaluation of novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives

Some novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. The results showed that most of the compounds exhibited promising activity (IC50 values in the range of 0.050-1.683 μM) than the reference drug metronidazole (IC50 = 1.78 μM). Active compounds were further screened for cytotoxicity against human embryonic kidney-293 (HEK-293) normal cell lines to ensure their toxic effect and the results revealed that active compounds were least toxic in the concentration range of 2.5-50 μM for 48 h and 2.5-25 μM for 72 h. At 100 μM for 48 h and at 50 μM for 72 h only four compounds 2c, 2h, 2k and 2l showed maximum viability and least cytotoxicity, respectively, concluding that all the screened compounds were least cytotoxic against human embryonic kidney-293 (HEK-293) normal cell lines in the concentration range of 2.5-50 and 2.5-25 μM.

Synthesis and reactivity of 2-pyrrolidino-, 2-N-methylpiperazino-, 2-piperidino-, and 2-morpholino-1,3,4-thiadiazines

A variety of 2-pyrrolidino-, 2-N-methylpiperazino-, 2-piperidino-, and 2-morpholino-1,3,4-thiadiazines were prepared by cyclocondensation of phenacyl halides with thiosemicarbazides. Heating of the products resulted in desulfurization and formation of pyrazoles. The rate of this process strongly depends on the substitution pattern of the 1,3,4-thiadiazines.

Synthesis of a new series of dithiocarbamate-linked peptidomimetics and their application in Ugi reactions

Novel peptidomimetics containing dithiocarbamate groups were synthesized via the Ugi reaction. Also, dithiocarbamates of natural amino acids were prepared and were used successfully in Ugi reactions to prepare novel peptidomimetics bearing amino acid and dithiocarbamate groups in a single structure. In addition the prepared dithiocarbamates based on amino acids are converted to the corresponding amides.

Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines

Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, 1H and 13C NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis.

Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica

The cyclization of chalcone with N-4 substituted thiosemicarbazides under basic condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. Structure-activity relationship shows that the compound with aromatic substituents at the thiocarbamoyl group was more active than those with the cyclic groups. However, it was clear from the IC50 values that the compounds 15 and 20 are more active and both showed a structural resemblance having an electron withdrawing groups attached to the phenyl ring. MTT assay showed that all the compounds are non-toxic to human kidney epithelial cell line.

Synthesis and characterization of a new series of hydroxy pyrazolines

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one obtained by Claisen-Schmidt condensation of 2-acetyl thiophene with benzaldehyde was converted into 2,3-dibromo-3-phenyl-1-(thiophen-2-yl)propan-1-one, which on treatment with various thiosemicarbazides in the presence of triethylamine in absolute ethanol, yielded the corresponding hydroxy pyrazolines 3a-h. All the compounds were characterized by IR, 1H NMR, and 13C NMR spectra. Copyright Taylor & Francis Group, LLC.

Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives

A series of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4]triazin-4-yl thiosemicarbazide derivatives 3-22 were prepared and evaluated in vitro against HM1:1MSS strain of Entamoeba histolytica, to identify the compounds for antiamoebic activity. They exhibited antiamoebic activity in the range (IC 50 = 0.81-7.31 μM). The results were compared to the activity of known drug metronidazole. It is inferred from the in vitro studies that the compounds 10, 11, 17 and 18 were found to be significantly better inhibitors of E. histolytica since IC50 values in the μM range elicited by these compounds are much lower than metronidazole. Besides, compounds 11 and 17 have shown the most promising antiamoebic activity (IC50 = 0.81 μM of 11, IC50 = 0.84 μM of 17 versus IC50 = 1.81 μM of metronidazole). The study suggests the possibility of developing triazine analogues as potential drug candidates for antiamoebic activity.