6954-50-3

Basic information

• Product Name: 2-isonicotinoyl-N-phenylhydrazinecarbothioamide
• Synonyms: 1-Phenyl-4-isonicotinoylthiosemicarbazide; N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarbothioamide
• CAS NO: 6954-50-3
• Molecular Formula: C₁₃H₁₂N₄OS
• Molecular Weight: 272.3256
• Mol File: 6954-50-3.mol

Chemical Properties

• Density: 1.357g/cm³
• Refractive Index: 1.705
• CAS DataBase Reference: 2-isonicotinoyl-N-phenylhydrazinecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-isonicotinoyl-N-phenylhydrazinecarbothioamide(6954-50-3)
• EPA Substance Registry System: 2-isonicotinoyl-N-phenylhydrazinecarbothioamide(6954-50-3)

Safety Data

• Hazardous Substances Data: 6954-50-3(Hazardous Substances Data)

Usage

Uses

Used in Cancer Treatment:
2-isonicotinoyl-N-phenylhydrazinecarbothioamide is used as an anti-cancer agent for its potential to inhibit the growth of cancer cells. It is being studied for its effectiveness in treating various types of cancer.
Used in Tuberculosis Treatment:
2-isonicotinoyl-N-phenylhydrazinecarbothioamide is used as an anti-tuberculosis agent for its potential to inhibit the growth of Mycobacterium tuberculosis, the bacteria responsible for causing tuberculosis.
Used in Leishmaniasis Treatment:
2-isonicotinoyl-N-phenylhydrazinecarbothioamide is used as a therapeutic agent for certain types of leishmaniasis, a parasitic disease transmitted by sand flies, for its potential to inhibit the growth of the Leishmania parasite.
Used in Antibacterial Applications:
2-isonicotinoyl-N-phenylhydrazinecarbothioamide is used as an antibacterial agent for its potential to inhibit the growth of bacteria, including drug-resistant strains, making it a promising candidate for the development of new antibiotics.

Upstream product

• 54-85-3 isoniazid 
• 103-72-0 phenyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 62-53-3 aniline 
• 5285-87-0 phenyl thiocyanate 

Downstream Products

• 33424-10-1 phenyl-(5-pyridin-4-yl[1,3,4]thiadiazol-2-yl)-amine 
• 1048370-11-1 N₄-(4,5-dioxo-3-phenyl-2-thioxo-1-imidazolidinyl)isonicotinamide 
• 1404079-98-6 2-dimethylaminomethyl-4-phenyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1404080-00-7 4-phenyl-5-pyridin-4-yl-2-(pyrrolidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1404080-01-8 N-methyl-N-[(4-phenyl-5-pyridin-4-yl-3-thioxo-2,4-dihydro-3H-1,2,4-triazol-2-yl)methyl]-2-aminoethanol 
• 1404080-03-0 2-[(4-chlorobenzylamino)methyl]-4-phenyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 552815-53-9 3-methylthio-4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazole 
• 1404079-92-0 3-[(pent-2-yl)thio]-4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazole 
• 1404079-93-1 3-[(pent-4-enyl)thio]-4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazole 
• 1404079-95-3 ethyl [4-phenyl-5-pyridin-4-yl-3-thioxo-2,4-dihydro-3H-1,2,4-triazol-2-yl]carboxylate 
• 1404079-97-5 2-hydroxymethyl-4-phenyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 16629-40-6 4-phenyl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1617-94-3 N-phenyl-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine 
• 16629-40-6 4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol 

Relevant articles and documents

A first-in-class anticancer dual HDAC2/FAK inhibitors bearing hydroxamates/benzamides capped by pyridinyl-1,2,4-triazoles

Novel 5-pyridinyl-1,2,4-triazoles were designed as dual inhibitors of histone deacetylase 2 (HDAC2) and focal adhesion kinase (FAK). Compounds 5d, 6a, 7c, and 11c were determined as potential inhibitors of both HDAC2 (IC50 = 0.09–1.40 μM) and F

Synthesis, characterization and cytotoxicity of new 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide and its metal complexes

The reaction of the newly synthesized ligand, 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide (H3L), with acetate salt of Co (II), Cu (II),Ni (II) and Zn (II) led to isolation of four solid complexes. The ligand and complexes structure elucidation were based on elemental analyses, spectral analyses (IR, UV–Visible, 1H and13C-NMR, MS and ESR), TGA, molar conductivity and magnetic moments measurements. The results indicated that the ligand exists in the thioketo form, while on coordination to the metal ions; it behaves as mono-negative bidentate chelate and exists in enol form. The optical band gap measurements of the ligand and its metal complexes are in the range 3.83–4.48?eV indicating their semi-conducting character. The cytotoxicity examination of H3L and its Zn (II) complex showed that the ligand have very strong cytotoxicity against both HCT-116 and HEPG-2 cell lines while, Zn (II) complex has moderate activity.

Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs

Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.

Synthetic nicotinic/isonicotinic thiosemicarbazides: In vitro urease inhibitory activities and molecular docking studies

Nicotinic and isonicotinic thiosemicarbazide or hydrazine carbothioamides 3–27 were synthesized and the structures of synthetic compounds were elucidated by various spectroscopic techniques such as EI-MS, 1H-, and 13C NMR. Synthetic derivatives were evaluated for their urease inhibitory activity which revealed that except few all derivatives demonstrated excellent inhibition in the range of IC50 values of 1.21–51.42 μM as compared to the standard thiourea (IC50 = 21.25 ± 0.13 μM). Among the twenty-five synthetic derivatives nineteen 1–5, 7, 8, 10, 12, 14–18, 20–22, 24–27 were found to be more active showing IC50 values between 1.13 and 19.74 μM showing superior activity than the standard. Limited structure-activity relationship demonstrated that the positions of substituent as well as position of nitrogen in pyridine ring are very important for inhibitory activity of this class of compound. To verify these interpretations, in silico study was also performed. A good correlation was obtained between the biological evaluation of active compounds and docking study.

Synthesis and molecular docking studies of glucose-linked isonicotinoyl- 1, 3, 4-thiadiazolidines as antitubercular agents

Background: The recent emergence of multidrug-resistant strains of M. tuberculosis that are resistant to two major effective drugs, viz. isoniazid and rifampicin, stimulated us to make an attempt for the development of a new class of potent antitubercular

Design, Synthesis and Antibacterial Evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione Hybrids

A new class of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin (CPFX)-1,2,4-triazole-5(4H)-thione hybrids 6a?–?6o was designed, synthesized and evaluated for their in?vitro antibacterial activities against a panel of clinically important drug-sensitive and d

Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2a-r) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data.

Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: Synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities

A series of quinoline based 1,3,4-oxadiazole derivatives (8a-l) were synthesized by a chloro-amine coupling reaction approach with different catalysts and solvents. Substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-substituted-N-phenylh

Synthesis and anti-Candidal activity of N-(4-aryl/cyclohexyl)-2-(pyridine- 4-yl carbonyl) hydrazinecarbothioamide

Eighteen N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide derivatives were synthesized, evaluated against ten clinical isolates of Candida spp. and compared with itraconazole. Introduction of p-chloro (2c), p-iodo (2q), m-chloro (2

Synthesis and crystal structure of 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4- triazole-5(4H)-thione

A triazole derivative i.e., 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole- 5(4H)-thione was synthesized and its structure was studied by X-ray diffraction. The crystals are orthorhombic, space group pbcn with a = 11.337 (2), b = 12.789 (3), c = 17.625 (4) ?