6610-29-3

Usage

Uses

Used in Analytical Chemistry:
4-Methylthiosemicarbazide is used as an analytical reagent for studying the electronic features of sulfur-containing compounds. It is particularly useful in high-resolution, low-temperature X-ray diffraction studies, which allow for the detailed examination of the molecular structure and bonding in these compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Methylthiosemicarbazide serves as an intermediate compound. Its unique structure and reactivity make it a valuable building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its ability to form complexes with metal ions can also be exploited in the development of new catalysts and ligands for organic reactions.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C2H7N3OS/c1-7-5-4-2(3)6/h5H,1H3,(H3,3,4,6)

Upstream product

• 556-61-6 methyl thioisocyanate 
• 144-54-7 N-methyldithiocarbamic acid 
• 18952-41-5 N-methylmethanethioamide 
• 471-32-9 dithiocarbonic acid hydrazide 
• 74-89-5 methylamine 
• 598-52-7 1-(methyl)-thiourea 
• 1544171-91-6 1,3-diethyl-4,5-bis(4-methylthiosemicarbazido)imidazolidin-2-one 
• 1544171-88-1 1,3-dimethyl-4,5-bis(4-methylthiosemicarbazido)imidazolidin-2-one 
• 7783-06-4 hydrogen sulfide 
• 5397-03-5 hydrazinecarbodithioic acid methyl ester 
• 75-15-0 carbon disulfide 
• 13037-11-1 S-methyl N-methyl dithiocarbamate 

Downstream Products

• 100057-69-0 acetic acid-[4-(4-methyl-thiosemicarbazonomethyl)-anilide] 
• 2613-12-9 benzaldehyde N⁴-methylthiosemicarbazone 
• 51146-63-5 4-methoxy-benzaldehyde-(4-methyl thiosemicarbazone) 
• 51236-93-2 (E)-2-(2-hydroxybenzylidene)-N-methylhydrazine-1-carbothioamide 
• 58064-65-6 1-(phenyl)carbonyl-4-(methyl)thiosemicarbazide 
• 364594-39-8 4-methyl-1-phenylcarbamoyl thiosemicarbazide 
• 154106-04-4 2-(4-methoxybenzoyl)-N-methylhydrazine-1-carbothioamide 
• 58064-52-1 1-formyl-4-methyl-3-thiosemicarbazide 
• 27421-65-4 acetophenone-4(N)-methylthiosemicarbazone 
• 108754-16-1 isopropylidene-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-hydrazine 
• 51146-59-9 (E)-N-methyl-2-(2-nitrobenzylidene)hydrazinecarbothioamide 
• 860002-19-3 1-(N-acetyl-sulfanilyl)-4-methyl thiosemicarbazide 
• 21817-92-5 3-methyl-4-(4-nitro-phenyl)-3H-thiazol-2-one hydrazone 
• 109965-28-8 Benzaldehyd-4,S-dimethylisothiosemicarbazon 

Relevant academic research and scientific papers

DNA cleavage, antimicrobial, spectroscopic and fluorescence studies of Co(II), Ni(II) and Cu(II) complexes with SNO donor coumarin Schiff bases

A series of Co(II), Ni(II) and Cu(II) complexes of the type ML2 have been synthesized with Schiff bases derived from methylthiosemicarbazone and 5-formyl-6-hydroxy coumarin/8-formyl-7-Hydroxy-4-methylcoumarin. The complexes are insoluble in common organic solvents but soluble in DMF and DMSO. The measured molar conductance values in DMF indicate that, the complexes are non-electrolytes in nature. In view of analytical, spectral (IR, UV-vis, ESR, FAB-mass and fluorescence), magnetic and thermal studies, it has been concluded that, all the metal complexes possess octahedral geometry in which ligand is coordinated to metal ion through azomethine nitrogen, thione sulphur and phenolic oxygen atom via deprotonation. The redox behavior of the metal complexes was investigated by using cyclic voltammetry. The Schiff bases and their complexes have been screened for their antibacterial (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi) and antifungal activities (Aspergillus niger, Aspergillus flavus and Cladosporium) by Minimum Inhibitory Concentration method. The DNA cleavage is studied by agarose gel electrophoresis method.

Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma

A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.

Preparation process of 4-methylthiosemicarbazide

The invention relates to a preparation process of 4-methylthiosemicarbazide, and belongs to the technical field of pharmaceutical chemicals. The preparation method comprises the following steps: adding hydrazine hydrate into a reaction bottle, dropwise adding carbon disulfide at 20-25 DEG C for 2-3 hours, and keeping the temperature at 20-25 DEG C for 1-2 hours after dropwise adding is finished; controlling the temperature to be 25-30 DEG C, dropwise adding monomethylamine into the reaction bottle for 1-2 hours, introducing nitrogen at the temperature of 70-75 DEG C after dropwise adding is finished, performing refluxing for 1-2 hours, and blowing off hydrogen sulfide gas generated by the reaction; and performing cooling to 0-5 DEG C, performing filtering to obtain an MTSC wet product, carrying out vacuum drying at 55 DEG C for 3 hours, performing heating to 70 DEG C, carrying out vacuum drying for 2-3 hours, and controlling the moisture content to be less than 0.1% to obtain white crystal powder 4-methylthiosemicarbazide. The preparation process is scientific and reasonable in design, wide in raw material source, low in cost, simple in step, green and pollution-free, improves theproduction efficiency, and is beneficial to industrial production.

A novel 8-nitro quinoline-thiosemicarbazone analogues induces G1/S & G2/M phase cell cycle arrest and apoptosis through ROS mediated mitochondrial pathway

A series of novel 8-nitro quinoline-based thiosemicarbazone analogues were synthesized and characterized by various spectroscopic and single crystal X-ray analyses. The potent antitumor effects of synthesized compounds towards the cancer cells were evaluated by MTT assay. Amongst, the compound 3a exhibited the highest inhibitory activity and the compounds 3f and 3b were also showed significant activity. The molecular mechanistic studies of cell death have demonstrated that the treated potent compound 3a induced G1/S & G2/M phase cell cycle arrest and induced apoptosis via mitochondrial dysfunction and increased the production of cytotoxic ROS levels. The RT-PCR gene expression analysis revealed that the cell death induced by activation of caspase-3 dependent intrinsic apoptotic signaling pathway. Further, the molecular binding affinity of compounds with estrogen receptor alpha was calculated by molecular docking studies. Thus, novel 8-nitro quinoline-thiosemicarbazone analogues provide a unique tool for breast cancer therapeutic tactics.

Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents

Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds are important fragments in medicinal chemistry because of their wide range of biological activities, including anticancer activities. The aim of this study was to determine the capacity of newly synthesized 1,3,4-thiadiazole compounds as chemotherapeutic agents. The structures of the obtained compounds were elucidated using 1H-NMR, 13C-NMR and mass spectrometry. Although the thiadiazole derivatives did not prove to be significantly cytotoxic to the tumour tissue cultures, compound 4i showed activity against the C6 rat brain cancer cell line (IC50 0.097 mM) at the tested concentrations.

Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity

A series of novel thiosemicarbazones including Schiff bases were synthesized by treatment of various aryl-substituted aldehydes with thiosemicarbazides in ethanol containing one drop of hydrochloric acid at reflux for 3–5 h. For this, thiosemicarbazides were obtained from hydrazine monohydrate and isothiocyanates in cold dry ethanol at 0 °C for 1 h. FT-IR, 1H NMR, 13C NMR, and LC–MS/MS spectroscopic methods and elemental analysis were used to characterize the identification of the synthesized products. The in vitro antioxidant activity of these compounds was tested by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical trapping method. All of the synthesized compounds showed lower antioxidant activity than the ascorbic acid standard and followed the sequence I > VII > X > VI > IV > IX > XI > II > V > III > VIII.

Anti-cancer, anti-oxidant and molecular docking studies of thiosemicarbazone indole-based derivatives

Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630?μM, comparable to the standard ascorbic acid (0.655?μM).

Inhibitory properties of aromatic thiosemicarbazones on mushroom tyrosinase: Synthesis, kinetic studies, molecular docking and effectiveness in melanogenesis inhibition

The group of 19 thiosemicarbazones (TSCs) were synthesized and its inhibitory activity toward mushroom tyrosinase and ability to inhibition of melanogenesis in B16 cells were investigated. Moreover, molecular docking of these compounds to the active site of the enzyme was performed. The obtained results allowed to make the structure-activity relationship (SAR) analysis. Kinetic studies revealed that TSCs 1, 2, 11 and 18 have better inhibitory properties than kojic acid, a reference compound, with the best inhibitory constant (Ki) value of 0.38 μM for TSC 2. According to SAR analysis, the smaller and less branched molecules exhibit higher affinity to the enzyme. Melanin production in B16 cells was inhibited by all investigated compounds at micromolar level. Most of compounds studied in this work can be considered as potent inhibitors of tyrosinase and melanogenesis. They may have broad application in food preservatives and cosmetics. Combined results of molecular docking and SAR analysis can be helpful in designing novel tyrosinase inhibitors of desired properties.

Isatin thiazoline hybrids as dual inhibitors of HIV-1 reverse transcriptase

A series of 3-3-{2-[2-3-methyl-4-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene]hydrazin-1-ylidene-2,3-dihydro-1H-indol-2-one derivatives has been designed and synthesized to study their activity on both HIV-1 (Human Immunodeficiency Virus type 1) RT (Reverse Transcriptase) associated functions. These derivatives are analogs of previously reported series whose biological activity and mode of action have been investigated. In this work we investigated the influence of the introduction of a methyl group in the position 3 of the dihydrothiazole ring and of a chlorine atom in the position 5 of the isatin nucleus. The new synthesized compounds are active towards both DNA polymerase and ribonuclease H in the μM range. The nature of the aromatic group in the position 4 of the thiazole was relevant in determining the biological activity.

Three nitrogen heterocycle containing 1, 2, 3 - thiadiazole - 5 - a amidine compounds and synthesis

The invention discloses an N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound with three aromatic rings of general formula TDCA and a synthesis method of N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound. The target compound of general formula TDCA is obtained by reacting a compound of general formula B and a compound of general formula A, wherein references of X and Y in the general formula A are the same as those in the general formula TDCA.