6957-92-2

Usage

Uses

Used in Agricultural Applications:
[(2,4-dichlorophenyl)methylideneamino]thiourea is used as a fungicide for [application reason] to protect plants from various fungal diseases. It inhibits the development and spread of fungal infections by interfering with the formation of fungal cell walls, thus preventing their growth and ensuring the health of crops.
Used in Crop Protection:
In the Crop Protection Industry, [(2,4-dichlorophenyl)methylideneamino]thiourea is used as a protective agent for [application reason] to safeguard crops from the detrimental effects of fungal infections. By controlling the spread of fungi, dichlorphenamid contributes to increased crop yields and improved agricultural productivity.
Used in Environmental Safety:
[(2,4-dichlorophenyl)methylideneamino]thiourea is used as a component in safety guidelines for [application reason] to ensure the proper handling and application of the fungicide. This helps minimize potential risks to human health and the environment, promoting responsible and sustainable agricultural practices.

InChI:InChI=1/C8H7Cl2N3S/c9-6-2-1-5(7(10)3-6)4-12-13-8(11)14/h1-4H,(H3,11,13,14)/b12-4+

Upstream product

• 874-42-0 2,4-dichlorobenzaldeyhde 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 106320-49-4 2,4-dichloro-benzaldehyde (4-oxo-5-propyl-thiazolidin-2-ylidene)-hydrazone 
• 100710-15-4 2,4-dichloro-benzaldehyde (5-butyl-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 132465-90-8 2,4-dichloro-benzaldehyde [5-(4-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 101081-20-3 2,4-dichloro-benzaldehyde [4-(4-bromo-phenyl)-5-oxo-thiazolidin-2-ylidene]-hydrazone 
• 101080-98-2 2,4-dichloro-benzaldehyde [4-(2,4-dichloro-phenyl)-5-oxo-thiazolidin-2-ylidene]-hydrazone 
• 28004-63-9 5-(2,4-dichloro-phenyl)-[1,3,4]thiadiazol-2-ylamine 
• 134951-56-7 [2-(2,4-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-thiourea 
• 134951-54-5 2-{[1-(2,4-Dichloro-phenyl)-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 128391-18-4 Cu⁽¹⁺⁾*C₈H₆Cl₂N₃S^(1-)={Cu(C₆H₃Cl₂CHNNCSNH₂)} 
• 1431555-44-0 4-[[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylimino]-methyl]phenol 

Relevant academic research and scientific papers

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs

A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]

Synthesis, antimicrobial and antioxidant evaluation with in silico studies of new thiazole Schiff base derivatives

A series of nineteen thiazole Schiff base derivatives 2a-2s were synthesized (Scheme 1) and elucidated by spectral analyses (IR, 1H NMR and HRMS). The evaluation of their antimicrobial activities against two gram-positive, two gram-negative, an

Thiosemicarbazones exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)

The superbug infection caused by metallo-β-lactamases (MβLs) carrying drug-resistant bacteria, specifically, New Delhi metallo-β-lactamase (NDM-1) has become an emerging threat. In an effort to develop novel inhibitors of NDM-1, thirteen thiosemicarbazones (1a-1m) were synthesized and assayed. The obtained molecules specifically inhibited NDM-1, with an IC50 in the range of 0.88–20.2 μM, and 1a and 1f were found to be the potent inhibitors (IC50 = 1.79 and 0.88 μM) using cefazolin as substrate. ITC and kinetic assays indicated that 1a irreversibly and non-competitively inhibited NDM-1 in vitro. Importantly, MIC assays revealed that these molecules by themselves can sterilize NDM-producing clinical isolates EC01 and EC08, exhibited 78-312-fold stronger activities than the cefazolin. MIC assays suggest that 1a (16 μg ml?1) has synergistic antimicrobial effect with ampicillin, cefazolin and meropenem on E. coli producing NDM-1, resulting in MICs of 4-32-, 4-32-, and 4-8-fold decrease, respectively. These studies indicate that the thiosemicarbazide is a valuable scaffold for the development of inhibitors of NDM-1 and NDM-1 carrying drug-resistant bacteria.

Design, synthesis, biological evaluation, QSAR analysis and molecular modelling of new thiazol-benzimidazoles as EGFR inhibitors

Heterocyclic rings such as thiazole and benzimidazole are considered as privileged structures, since they constitute several FDA-approved drugs for cancer treatment. In this work, a new set of 2-(2-(substituted) hydrazinyl)-4-(1-methyl-1H-benzo[d]imidazol-2-yl) thiazoles 4a-q were designed as epidermal growth factor receptor (EGFR) inhibitors and synthesized using concise synthetic methods. The new target compounds have been evaluated in vitro for their suppression activity against EGFR TK. Compounds 4n, 4h, 4i, 4a and 4d exhibited significant potency in comparison with erlotinib which served as a reference drug (IC50, 71.67–152.59 nM; IC50 erlotinib, 152.59 nM). Furthermore, MTT assay revealed that compounds 4j, 4a, 4f, 4h, 4n produced the most promising cytotoxic potency against the human breast cancer cell line (MCF-7) (IC50; 5.96–11.91 μM; IC50 erlotinib; 4.15 μM). Compound 4a showed promising activity as EGFR TK inhibitor as well as anti-breast cancer agent. In addition, 4a induced apoptotic effect and cell cycle arrest at G2/M phase preventing the mitotic cycle in MCF-7 cells. Moreover, 4a upregulated the oncogenic parameters; caspase-3, p53, Bax/Bcl-2 as well as it inhibited the level of PARP-1 enzyme. QSAR study was carried out for the new derivatives and it revealed the goodness of the models. Furthermore, molecular docking studies represented the binding modes of the promising compounds in the active pocket of EGFR.

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin

Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs

α-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1–13) and 2-amino-thiadiazole based Schiff bases (14–22) were synthesized, characterized by 1H NMR and HREI-MS and screened for α-glucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of α-glucosidase inhibitory potential with IC50 values ranging between 2.30 ± 0.1 to 38.30 ± 0.7 μM, when compare with standard drug acarbose having IC50 value of 39.60 ± 0.70 μM. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding α-glucosidase inhibitory potential with IC50 values of 3.30 ± 0.1, 5.80 ± 0.2, 2.30 ± 0.1, 2.70 ± 0.1, 2.30 ± 0.1, 5.50 ± 0.1, 4.70 ± 0.2, and 5.50 ± 0.2 μM respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent α-glucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking.

2 - (2 - Animal pen asia jingjing base) -5 - acyl thiazole and its medical use (by machine translation)

The invention formula I shown by 2 - (2 - animal pen asia jingjing base) - 5 - acyl thiazole and its pharmaceutically acceptable salt, pharmaceutical composition and thereof in the preparation of influenza virus neuraminidase inhibitors in the application. Wherein R is selected from: methyl, ethyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl; R1 Is selected from: hydrogen, C1 - C2 Alkyl, C3 - C4 Straight-chain or C3 - C4 Branched alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, bromomethyl, [...], three bromine methyl, chloromethyl, dichloro methyl or trichloromethyl; X1 , X5 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl; X2 , X4 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, C3 - C4 Straight or branched chain alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl; X3 Is selected from: hydrogen, deuterium, C1 - C2 Alkyl, hydroxy, methoxy, ethoxy, fluoro, chloro, bromo, iodo, nitro, amino, methylamino, dimethylamino, acetyl, carboxy, methoxycarbonyl or ethoxycarbonyl. (by machine translation)

2 - (2 - animal pen Asia jingjing base) - 5 - (1, 2, 4 - triazole - 1 - yl) thiazole and its preparation and use

The invention relates to 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole represented by chemical structural formula I, or salts thereof. According to the chemical structural formula I, R is selected from hydrogen, deuterium, C1-C2 alkyl, and C3-C4 linear alkyl or branched alkyl; and X1-X5 are selected from hydrogen, deuterium, C1-C2 alkyl, hydroxyl, methoxyl, ethyoxyl, fluorine, chlorine, bromine, and nitryl. The invention also discloses applications of 2-(2-benzylidene hydrazino)-5-(1,2,4-triazole-1-yl)thiazole in preparing influenza neuraminidase inhibitors.

Synthesis, antioxidant, antifungal, molecular docking and ADMET studies of some thiazolyl hydrazones

Some thiazolyl hydrazones were synthesized by one pot reaction of thiophene-2-carbaldehyde or 2, 4-dichlorobenzaldehyde, thiosemicarbazide and various phenacyl bromides which were preliminarily screened for in vitro antioxidant and antifungal activities.

Novel 4-thiazolidinones as non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA polymerase

In continuation of our efforts to develop new derivatives as hepatitis C virus (HCV) NS5B inhibitors, we synthesized novel 5-arylidene-4-thiazolidinones. The novel compounds 29-42, together with their synthetic precursors 22-28, were tested for HCV NS5B inhibitory activity; 12 of these compounds displayed IC50 values between 25.3 and 54.1 μM. Compound 33, an arylidene derivative, was found to be the most active compound in this series with an IC50 value of 25.3 μM. Molecular docking studies were performed on the thumb pocket-II of NS5B to postulate the binding mode for these compounds.