5351-70-2

Basic information

• Product Name: Cinnamaldehyde thiosemicarbazone
• Synonyms: 1-(3-Phenyl-2-propenylidene)thiosemicarbazide;1-(3-Phenylallylidene)thiosemicarbazide;3-Phenylpropenalthiosemicarbazone;3-phenylacrylaldehyde thiosemicarbazone;[(E)-[(E)-3-phenylprop-2-enylidene]amino]thiourea
• CAS NO: 5351-70-2
• Molecular Formula: C₁₀H₁₁N₃S
• Molecular Weight: 205.28
• Mol File: 5351-70-2.mol

Chemical Properties

• Melting Point: 139 °C
• Boiling Point: 363°Cat760mmHg
• Flash Point: 173.3°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Refractive Index: 1.598
• PKA: 11.61±0.70(Predicted)
• CAS DataBase Reference: Cinnamaldehyde thiosemicarbazone(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamaldehyde thiosemicarbazone(5351-70-2)
• EPA Substance Registry System: Cinnamaldehyde thiosemicarbazone(5351-70-2)

Safety Data

• Hazardous Substances Data: 5351-70-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cinnamaldehyde thiosemicarbazone is used as a potential drug candidate for the development of new treatments due to its demonstrated antimicrobial, antitumor, antiviral, and antioxidant properties. Its multifaceted biological activities suggest that it could be instrumental in addressing a range of health conditions and diseases.
Used in Antimicrobial Applications:
In the field of antimicrobial research, cinnamaldehyde thiosemicarbazone is utilized for its ability to combat various microorganisms. This makes it a valuable asset in the ongoing battle against antibiotic-resistant bacteria and other pathogens.
Used in Antitumor Applications:
Cinnamaldehyde thiosemicarbazone is employed as an antitumor agent, where it may contribute to the development of novel cancer therapies. Its potential to target and inhibit the growth of tumor cells makes it a promising compound for further investigation in oncology.
Used in Antiviral Applications:
Cinnamaldehyde thiosemicarbazone is also used in antiviral applications, where it may help in the creation of treatments for viral infections. Its antiviral properties could be harnessed to develop new medications to combat a variety of viral diseases.
Used in Antioxidant Applications:
Cinnamaldehyde thiosemicarbazone is used for its antioxidant capabilities, which can be beneficial in the development of products that protect against oxidative stress and related conditions. This may include applications in both medicine and the cosmetics industry.
Overall, cinnamaldehyde thiosemicarbazone's diverse range of potential uses underscores the importance of continued research and development to fully realize its benefits and applications across various industries.

InChI:InChI=1/C10H11N3S/c11-10(14)13-12-8-4-7-9-5-2-1-3-6-9/h1-8H,(H3,11,13,14)

Upstream product

• 79-19-6 thiosemicarbazide 
• 104-55-2 3-phenyl-propenal 
• 4346-94-5 thiosemicarbazide hydrochloride 

Downstream Products

• 28004-54-8 2-amino-5-styryl-1,3,4-thiadiazole 
• 134834-80-3 C₁₅H₁₄N₄O₃S*BrH 
• 151921-24-3 1-allylphenylidene-4-(N-antipyrinyl-glycyl)-3-thiosemicarbazone 
• 73923-56-5 3-phenyl-propenal (4,5-diphenyl-thiazol-2-yl)-hydrazone 
• 51680-05-8 5-acetylamino-2-styryl-1,3,4-thiadiazole 
• 134834-88-1 1-[1-Acetyl-3-(5-nitro-furan-2-ylmethylsulfanyl)-5-((Z)-styryl)-1,5-dihydro-[1,2,4]triazol-4-yl]-ethanone 
• 73923-65-6 2-[5-(4,5-diphenyl-thiazol-2-yl)-3-styryl-formazan-1-yl]-benzoic acid 
• 357639-18-0 1-(4-(4-bromophenyl)thiazol-2-yl)-2-(3-phenylallylidene)hydrazine 
• 618064-77-0 1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(3-phenylallylidene)hydrazine 
• 114554-95-9 [(3-phenyl-2-propenylidene)hydrazono]thiazolidin-4-one 
• 1226451-88-2 Cl₃Sb*C₁₀H₁₁N₃S 
• 351444-21-8 3-phenyl-2-propenal-[4-(4-chlorophenyl)-2-thiazolyl]hydrazone 

Relevant articles and documents

Design, synthesis, and cytotoxicity screening of new synthesized imidazolidine-2-thiones as VEGFR-2 enzyme inhibitors

A series of imidazolin-2-thione derivatives was synthesized and structurally confirmed through the use of different spectroscopic techniques such as infrared, nuclear magnetic resonance, and mass spectrometry along with elemental analyses. The breast canc

Green and Facile Synthesis of New 3-(Phenylallylideneamino)indeno[1,2-d]imidazoles

A green and facile strategy has been proposed for the synthesis of previously unknown 3a,8a-dihydroxy-3-[(3-phenylprop-2-en-1-ylidene)amino]-2-sulfanylidene-2,3,3a,8a-tetrahydro-1H-indeno[1,2-{und}]imidazol-8-one and 3a,8a-dihydroxy-3-[(3-phenylprop-2-en-

PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles

A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.

Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives

In the search for new antifungal agents, a novel series of fifteen hydrazine-thiazole derivatives was synthesized and assayed in vitro against six clinically important Candida and Cryptococcus species and Paracoccidioides brasiliensis. Eight compounds showed promising antifungal activity with minimum inhibitory concentration (MIC) values ranging from 0.45 to 31.2 μM, some of them being equally or more active than the drug fluconazole and amphotericin B. Active compounds were additionally tested for toxicity against human embryonic kidney (HEK-293) cells and none of them exhibited significant cytotoxicity, indicating high selectivity. Molecular modeling studies results corroborated experimental SAR results, suggesting their use in the design of new antifungal agents.

Thiosemicarbazones as Aedes aegypti larvicidal

Abstract A set of aryl- and phenoxymethyl-(thio)semicarbazones were synthetized, characterized and biologically evaluated against the larvae of Aedes aegypti (A. egypti), the vector responsible for diseases like Dengue and Yellow Fever. (Q)SAR studies were useful for predicting the activities of the compounds not included to create the QSAR model as well as to predict the features of a new compound with improved activity. Docking studies corroborated experimental evidence of AeSCP-2 as a potential target able to explain the larvicidal properties of its compounds. The trend observed between the in silico Docking scores and the in vitro pLC50 (equals -log LC50, at molar concentration) data indicated that the highest larvicidal compounds, or the compounds with the highest values for pLC50, are usually those with the higher docking scores (i.e., greater in silico affinity for the AeSCP-2 target). Determination of cytotoxicity for these compounds in mammal cells demonstrated that the top larvicide compounds are non-toxic.

Structure-activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei

To explore the structure-activity relationships of thiosemicarbazones on African trypanosome: Trypanosoma brucei brucei, a series of thirty-five thiosemicarbazones (1-35) have been synthesized and characterized by their 1H NMR, 13C NMR, and FT-IR spectra. All compounds were tested for trypanocidal activity using the method "Lilit alamar blue". The comparison of trypanocidal power of thiosemicarbazones was performed considering their structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl) ethylidene-4-phenyl- thiosemicarbazide (34). With a trypanocidal activity of 3.97 μM, this compound is the most active of the series.

Studies toward the structural optimization of novel thiazolylhydrazone- based potent antitrypanosomal agents

In previous studies, we identified promising anti-Trypanosoma cruzi cruzain inhibitors based on thiazolylhydrazones. To optimize this series, a number of medicinal chemistry directions were explored and new thiazolylhydrazones and thiosemicarbazones were

Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring

A series of arylidene-2-(4-(4-methoxy/bromophenyl) thiazol-2-yl) hydrazines (4a-z) and 1-(4-(4-methoxy/bromophenyl) thiazol-2-yl)-2-cyclohexylidene/cyclopentylidene hydrazines (5a-b/6a-b) were synthesized, characterized and screened for their antimicrobial activities. The structures of synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analyses. Both the anti-bacterial and anti-fungal activities with MIC values of compounds were evaluated. The results of anti-bacterial screening reveal that among all the compounds screened eight compounds showed moderate to good anti-bacterial activity while ten of the newly synthesized compounds displayed good to excellent anti-fungal activity. Among the tested compounds, the most effective compounds with MIC value in the range of 6.25-25 μg/ml are 4a, 4n, 4z, 5a, 5b, 6a and 6b against three fungal strains viz. Candida albicans, Cryptococcus neoformans and Aspergillus flavus.

A class of potent tyrosinase inhibitors: Alkylidenethiosemicarbazide compounds

A series of alkylidenethiosemicarbazide compounds were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that most of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 1f was found to be the most potent inhibitor with IC50 value of 0.086 μM, suggesting that further development of such compounds may be of interest.

Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones

A series of novel 3-[5-substituted phenyl-1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones were synthesized and evaluated for anticonvulsant, sedative-hypnotic and CNS depressant activities. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight 2-styrylquinazolin-4(3H)-one derivatives were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. The neurotoxicity was assessed using the rotorod method. Out of eighteen compounds only 4a, 4d, 4e, 4j and 4k showed anticonvulsant activity in one or more test models. All except 4e and 4f exhibited significant sedative-hypnotic activity via actophotometer screen. CNS depressant activity screened with the help of the forced swim pool method resulted into some potent compounds. From the experimental observation it can be concluded that synthesized compounds exhibited relatively better sedative-hypnotic and CNS depressant activities.