N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide

Base Information

• Chemical Name: N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide
• CAS No.: 104-06-3
• Molecular Formula: C10H12 N4 O S
• Molecular Weight: 236.297
• Hs Code.: 29309090
• European Community (EC) Number: 203-170-6
• Nikkaji Number: J5.023G
• Wikipedia: Thioacetazone
• Wikidata: Q7784646
• Mol file: 104-06-3.mol

Synonyms:Thiosemicarbazone;Thiosemicarbazones

Chemical Property of N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide

Chemical Property:

• Melting Point: 225-230 °C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 11.35±0.70(Predicted)
• Flash Point: °C
• PSA: 111.60000
• Density: 1.3g/cm³
• LogP: 1.97630
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 236.07318219
• Heavy Atom Count: 16
• Complexity: 285

Purity/Quality:

99%, ^*data from raw suppliers

Thiacetazone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)C=NNC(=S)N
• Isomeric SMILES: CC(=O)NC1=CC=C(C=C1)/C=N\NC(=S)N
• Uses: Thiacetazone (cas# 104-06-3) is used in combination chemotherapy, in preparation of nucleosides as inhibitors of adenylate-forming enzyme MenE.
• Indications: Thiacetazone is active against many strains of M. tuberculosis. It is not marketed in the United States. However, because of its low cost, it is used as a first-line agent in East Africa, especially in combination with compounds such as isoniazid. The most common side effects of thiacetazone include GI intolerance and development of rashes. It causes significant ototoxicity, especially when coadministered with streptomycin. Lifethreatening hypersensitivity reactions, such as hepatitis, transient marrow aplastic syndromes, neutropenia, and thrombocytopenia, have been reported.

Technology Process of N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide

There total 5 articles about N-(4-((2-Carbamothioylhydrazono)methyl)phenyl)acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

para-acetamidobenzaldehyde (122-85-0) → N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide (104-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N₂H₄

With hydrazine;

DOI:10.1021/ja01101a504

Reference yield:

4-acetylamino-benzaldehyde hydrazone + ammonium thiocyanate (1147550-11-5) → N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide (104-06-3)

Guidance literature:

DOI:10.1021/ja01150a527 DOI:10.1021/ja01101a504

Reference yield:

(E)-2-(4-aminobenzylidene)hydrazinecarbothioamide (6957-91-1) + acetic anhydride (108-24-7) → N-(4-[2-(aminocarbonothionyl)hydrazono]methylphenyl)acetamide (104-06-3)

Guidance literature:

upstream raw materials:

ammonium thiocyanate

(E)-2-(4-aminobenzylidene)hydrazinecarbothioamide

acetic anhydride

para-acetamidobenzaldehyde

Downstream raw materials:

acetic acid-[4-(thiazol-2-ylhydrazono-methyl)-anilide]

acetic acid-{4-[4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-thiazol-2-ylhydrazonomethyl]-anilide}

N,N'''-bis-(4-acetylamino-benzylidene)-μ-disulfido-dicarboxamidrazone

1-(4-acetylamino-benzyl)-thiosemicarbazide

Refernces

Synthesis, characterization, antitumor, and cytotoxic activity of mononuclear Ru(II) complexes

10.1080/00958972.2010.534140

The research focuses on the synthesis, characterization, and evaluation of the antitumor and cytotoxic activities of a series of mononuclear Ru(II) complexes, specifically [Ru(T)2(S)]2t, where T represents 2,2'-bipyridine or 1,10-phenanthroline, and S denotes various thiosemicarbazone derivatives such as CH3-bitsz, Cl-bitsz, Br-bitsz, tmtsz, and dmtsz. The reactants used in the synthesis include hydrated ruthenium trichloride, 2,2'-bipyridine, 1,10-phenanthroline, and the thiosemicarbazone ligands. The complexes were characterized using UV-Vis, IR, 1H-NMR, FAB-mass spectroscopy, and elemental analysis. The antitumor activity was assessed in vivo against a transplantable murine tumor cell line (Ehrlich’s ascitic carcinoma), and the cytotoxic activity was evaluated in vitro against human cancer cell lines (Molt 4/C8 and CEM) and a murine tumor cell line (L1210). The study aimed to develop potential cytotoxins and explore the antitumor properties of these Ru(II) complexes as alternatives to platinum-based drugs, which are known for their high toxicity.

Antitumor activity of (-)-α-bisabolol-based thiosemicarbazones against human tumor cell lines

10.1016/j.ejmech.2010.03.026

The research focused on the synthesis and evaluation of antitumor activity of thiosemicarbazones derived from the natural sesquiterpene (±)-α-bisabolol against a panel of eight human tumor cell lines. The purpose was to assess their potential as anti-cancer agents and to identify structure-activity relationships that contribute to their antitumor activity. The study concluded that some of the synthesized compounds, particularly the ketone derivative 3l, exhibited potent antitumor activity and high selectivity for myeloid leukemia cells (K-562), with compound 3l showing superior activity compared to the standard drug doxorubicin. The chemicals used in the process included (±)-α-bisabolol, isothiocyanate, hydrazine, and various benzaldehyde derivatives, as well as acetophenone or benzophenone, with catalytic amounts of sulfuric acid used in the reaction. The synthesized thiosemicarbazones were then tested for their inhibitory effects on cancer cell growth, leading to the identification of structural requirements for enhanced antitumor activity.

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