5446-18-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichlorophenylhydrazine hydrochloride is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its reactivity allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 2,4-Dichlorophenylhydrazine hydrochloride serves as a key building block for the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical entities.
Used in Synthesis of Pyrazole Analogues of Curcumin:
2,4-Dichlorophenylhydrazine hydrochloride is specifically utilized in the synthesis of pyrazole analogues of curcumin, which are compounds with potential anti-inflammatory, antioxidant, and anticancer properties. 2,4-Dichlorophenylhydrazine hydrochloride's role in this process highlights its importance in the development of novel therapeutic agents.

InChI:InChI=1/C6H6Cl2N2.ClH/c7-4-1-2-6(10-9)5(8)3-4;/h1-3,10H,9H2;1H

Upstream product

• 554-00-7 2,4-Dichloroaniline 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 99602-27-4 1,1-dichloro-2-(2,4-dichlorophenylazo)ethene 
• 408539-08-2 2,3-dichloro-crotonaldehyde-(2,5-dichloro-phenylhydrazone) 
• 857816-75-2 acetic acid-[(2,3-dichloro-but-2-enylidene)-(2,4-dichloro-phenyl)-hydrazide] 
• 14657-26-2 1-(2,4-dichloro-phenyl)-semicarbazide 
• 106103-85-9 (2,4-dichloro-phenylhydrazono)-acetic acid 
• 116599-88-3 1-(2,4-dichloro-anilino)-2-methyl-4,6-diphenyl-pyridinium; chloride 
• 24725-64-2 2,3,4,4-Tetrachlor-1-<2,4-dichlor-phenylazo>-buta-1,3-dien 
• 73569-32-1 2,3-Bis-[(2,4-dichloro-phenyl)-hydrazono]-propan-1-ol 
• 77635-92-8 N-(2,4-Dichloro-phenyl)-N'-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-hydrazine 
• 77635-75-7 4-{1-[(2,4-Dichloro-phenyl)-hydrazono]-ethyl}-benzonitrile 
• 77635-54-2 2-{1-[(2,4-Dichloro-phenyl)-hydrazono]-ethyl}-4,5-dimethyl-phenol 
• 77635-63-3 N-(2,4-Dichloro-phenyl)-N'-[1-(2-trifluoromethyl-phenyl)-eth-(E)-ylidene]-hydrazine 
• 152713-60-5 5-Butyl-4-(2'-cyano-biphenyl-4-ylmethyl)-2-(2,4-dichloro-phenyl)-2H-pyrazole-3-carboxylic acid ethyl ester 
• 77635-87-1 N-(2,4-Dichloro-phenyl)-N'-[1-(4-fluoro-phenyl)-eth-(E)-ylidene]-hydrazine 

Relevant academic research and scientific papers

Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode

A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.

Discovery of 1,3,4-oxadiazol-2-one-containing benzamide derivatives targeting FtsZ as highly potent agents of killing a variety of MDR bacteria strains

The spread of infections caused by multidrug-resistant (MDR) pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA), has created a need for new antibiotics with novel mechanisms of action. The bacterial division protein FtsZ has been identified as a novel drug target that can be exploited clinically. As part of an ongoing effort to develop FtsZ-targeting antibacterial agents, we describe herein the design, synthesis and bioactivity of six series of novel 1,3,4-oxadiazol-2-one-containing, 1,2,4-triazol-3-one-containing and pyrazolin-5-one-containing benzamide derivatives. Among them, compound A14 was found to be the most potent antibacterial agent, much better than clinical drugs such as ciprofloxacin, linezolid and erythromycin against all the tested gram-positive strains, particularly methicillin-resistant, penicillin-resistant and clinical isolated S. aureus. Subsequent studies on biological activities and docking analyses proved that A14 functioned as an effective compound targeting FtsZ. Preliminary SAR indicated a general direction for further optimization of these novel analogues. Taken together, this research provides a promising chemotype for developing newer FtsZ-targeting bactericidal agents.

Design, synthesis and biological activities of novel benzoyl hydrazines containing pyrazole

In search of environmentally benign compounds with high biological activity, low toxicity and low resistance, 8 novel benzoyl hydrazines containing pyrazole were designed and synthesized. All compounds were characterized by 1H NMR spectra and HRMS. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L -1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Eight novel benzoyl hydrazines containing pyrazole were designed and synthesized. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L-1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Copyright

Design, Synthesis, and 3D-QSAR Analysis of Novel 1,3,4-Oxadlazol-2(3H)-ones as Protoporphyrlnogen Oxidase Inhibitors

Protoporphyrlnogen oxidase (PPO, EC 1.3.3.4) has been Identified as one of the most significant action targets for a large chemically diverse family of herbicides that exhibit some Interesting characteristics, such as low use rate, low toxicity to mammals, and low environmental Impact. As a continuation of research work on the development of new PPO Inhibitors, some benzothlazole analogues of oxadlargyl, an Important PPO-lnhlbltlng commercial herbicide, were designed and synthesized by ring-closing of the substltuents at the C-4 and C-5 positions. The bloassay results Indicated that the series 8, 9, and 10 have good PPO Inhibition activity with kl values ranging from 0.25 to 18.63 μM. Most Interestingly, 9I, ethyl 2-((5-(5-fert-butyl-2-oxo-1,3,4-oxadlazol- 2(3H)-yl)-6fluorobenzothlazol-2-yl)sulfanyl) propanoate, was Identified as the most promising candidate due to Its high PPO Inhibition effect (kl 1.42 ,μM) and broad spectrum postemergence herbicidal activity at the concentration of 37.5 g of al/ha.

PHARMACEUTICAL COMPOUNDS

Condensed tricyclic compounds having a condensed structure containing one phenyl and one pyrazole ring linked with each other by a central ring comprising from five to eight atoms, having affinity for the CB1 and/or CB2 receptors, with central nervous system and/or peripheral activity, of formula (I): wherein the various substituents are as defined in the description. The compounds show affinity for the CB1 and/or CB2 cannabinoidergic receptors.