20443-39-4

Usage

Uses

Used in Pharmaceutical Research:
2-(Chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structural features and potential biological activity. Its presence in drug molecules can contribute to enhanced pharmacological properties, such as improved binding affinity and selectivity towards target proteins or receptors.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(Chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole serves as a versatile building block for the creation of diverse organic molecules. Its reactivity and functional groups enable chemists to perform various chemical reactions, leading to the formation of new compounds with potential applications in various industries.
Used in Medicinal Chemistry:
2-(Chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole is employed as a structural motif in the design and development of new drugs and pharmaceutical products. Its incorporation into drug candidates can enhance their pharmacokinetic and pharmacodynamic properties, such as solubility, stability, and bioavailability, ultimately improving their therapeutic efficacy.
It is crucial to handle 2-(Chloromethyl)-1-methyl-5-nitro-1H-1,3-benzodiazole with care and adhere to proper safety protocols when working with it in a laboratory setting to ensure the safety of researchers and the integrity of the experiments.

InChI:InChI=1/C9H8ClN3O2/c1-12-8-3-2-6(13(14)15)4-7(8)11-9(12)5-10/h2-4H,5H2,1H3

Upstream product

• 79-04-9 chloroacetyl chloride 
• 41939-61-1 N₁-methyl-4-nitrobenzene-1,2-diamine 
• 79-11-8 chloroacetic acid 

Downstream Products

• 1425845-76-6 1-(4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)-phenyl)ethanone 
• 1425845-78-8 propyl 4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)benzoate 
• 1425845-80-2 2-((4-fluorophenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole 
• 1425845-82-4 2-((4-chlorophenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole 
• 1425845-84-6 4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)benzaldehyde 
• 1425845-86-8 2-((4-allyl-2-methoxyphenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole 
• 1425845-90-4 ethyl 4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)benzoate 
• 1425845-92-6 methyl 4-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)benzoate 
• 1425845-94-8 2-((4-(tert-butyl)phenoxy)methyl)-1-methyl-5-nitro-1H-benzo[d]imidazole 
• 1425845-96-0 1-methyl-5-nitro-2-(phenoxymethyl)-1H-benzo[d]imidazole 
• 1425845-72-2 1-(3-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)-phenyl)ethanone 
• 1425845-74-4 1-(2-((1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)methoxy)-phenyl)ethanone 

Relevant academic research and scientific papers

Novel methyl indolinone-6-carboxylates containing an indole moiety as angiokinase inhibitors

A novel series of methyl indolinone-6-carboxylates bearing an indole moiety were identified as potent angiokinase inhibitors. The most active compound, A8, potently targeted the kinase activities of vascular endothelial growth factor receptors 2 and 3, and platelet-derived growth factor receptors α and β, with IC50 values in the nanomolar range. In addition, A8 effectively suppressed the proliferation of human umbilical vein endothelial cells, and HT-29 and MCF-7 cancer cells, by inducing apoptosis. Compound A8 is thus a promising candidate for further investigation.

Synthesis and antifungal activity of 2-chloromethyl-1 H -benzimidazole derivatives against phytopathogenic fungi in vitro

A series of 35 benzimidazole derivatives were synthesized from 2-chloromethyl-1H-benzimidazole in good yields. Their structures were characterized by 1H and 13C NMR and HRESIMS. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Compound 4m displayed strong growth inhibition of C. gloeosporioides, A. solani, and F. solani with IC50 of 20.76, 27.58, and 18.60 μg/mL, respectively. Selective inhibition of B. cinerea instead of the other fungal pathogenes was observed with 7f (IC50 of 13.36 μg/mL), comparable to that of positive control, a commercial agricultural fungicide hymexazol (IC50 of 8.92 μg/mL). Compound 5b exhibited remarkable antifungal properties against Cytospora sp., C. gloeosporioides, B. cinerea, and F. solani with IC50 values of 30.97, 11.38, 57.71, and 40.15 μg/mL, respectively; among the target fungi, 5b was the most active compound and superior to the reference against C. gloeosporioides alone. Structure-activity relationship (SAR) data of these compounds are as follows: (1) introduction of the chlorine atom on para-position in the benzene ring help to increase activity (4f vs 4c; 7f vs 7n), (2) the sulfonyl group is critical for the inhibition of C. gloeosporioides (5b and 5c vs 5a), and (3) the unsubstituted benzene ring improve activity (4m vs 4n, 4e and 4a). Thus, compounds 5b, 4m, and 7f emerged as a new leading structure for the development of new fungicides.