228419-13-4

Basic information

• Product Name: 3-BENZYLOXYBENZHYDRAZIDE
• Synonyms: 3-BENZYLOXYBENZHYDRAZIDE;3-BENZYLOXYBENZOHYDRAZIDE
• CAS NO: 228419-13-4
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.27
• Mol File: 228419-13-4.mol

Chemical Properties

• Melting Point: 113 °C
• Appearance: /
• Density: 1.201 g/cm³
• Refractive Index: 1.61
• CAS DataBase Reference: 3-BENZYLOXYBENZHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZYLOXYBENZHYDRAZIDE(228419-13-4)
• EPA Substance Registry System: 3-BENZYLOXYBENZHYDRAZIDE(228419-13-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 228419-13-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Benzyloxybenzhydrazide is utilized as a key building block for the creation of various pharmaceuticals, leveraging its reactivity to form complex molecular structures that can address specific medical needs.
Used in Organic Compounds Synthesis:
In the realm of organic chemistry, 3-Benzyloxybenzhydrazide is employed as a versatile component in the synthesis of a wide array of organic compounds, contributing to the development of new materials and chemical entities.
Used in Medicinal Chemistry Research:
As a reagent in medicinal chemistry, 3-Benzyloxybenzhydrazide aids researchers in exploring novel chemical pathways and mechanisms, potentially leading to the discovery of new drugs and therapeutic agents.
Used in Drug Discovery and Development:
3-BENZYLOXYBENZHYDRAZIDE's potential in drug discovery and development is significant, as it can be integrated into the design and synthesis of new molecular entities with potential therapeutic effects.
Used in Synthesis of Biologically Active Molecules:
3-Benzyloxybenzhydrazide is also used in the synthesis of biologically active molecules, which can have implications in various biological and medical applications, including the treatment of diseases and the enhancement of biological processes.

InChI:InChI=1/C14H14N2O2/c15-16-14(17)12-7-4-8-13(9-12)18-10-11-5-2-1-3-6-11/h1-9H,10,15H2,(H,16,17)

Upstream product

• 100-44-7 benzyl chloride 
• 61535-46-4 3-benzyloxy-benzoyl chloride 
• 69026-14-8 3-benzyloxybenzoic acid 
• 7781-98-8 ethyl-3-hydroxybenzoate 
• 100-39-0 benzyl bromide 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 63888-94-8 ethyl 3-(benzyloxy)benzoate 

Downstream Products

• 228419-14-5 5-(3-benzyloxyphenyl)-1,3,4-oxadiazol-2-one 
• 5378-29-0 2-(3-hydroxyphenyl)-1,3,4-oxadiazole 
• 79302-77-5 2-(3-hydroxyphenyl)-1,3,4-oxadiazol-5-one 
• 741262-95-3 5-[3-benzyloxyphenyl]-1,3,4-oxadiazole-2(3H)-thione 
• 190661-08-6 2-carbohydrazide 
• 443296-90-0 3-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide 

Relevant articles and documents

Substitution of terminal amide with 1H-1,2,3-triazole: Identification of unexpected class of potent antibacterial agents

3-Methoxybenzamide (3-MBA) derivatives have been identified as novel class of potent antibacterial agents targeting the bacterial cell division protein FtsZ. As one of isosteres for the amide group, 1,2,3-triazole can mimic the topological and electronic features of the amide, which has gained increasing attention in drug discovery. Based on these considerations, we prepared a series of 1H-1,2,3-triazole-containing 3-MBA analogues via isosteric replacement of the terminal amide with triazole, which had increased antibacterial activity. This study demonstrated the possibility of developing the 1H-1,2,3-triazole group as a terminal amide-mimetic element which was capable of both keeping and modulating amide-related bioactivity. Surprisingly, a different action mode of these new 1H-1,2,3-triazole-containing analogues was observed, which could open new opportunities for the development of antibacterial agents.

New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site

A series of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides were tailored and synthesized as new potent inhibitors of tyrosinase. The rationale for inhibitor design was based on the active site structural evidence from the crystal structures of bacterial tyrosinase and potato catechol oxidase enzymes. Kinetic and active site binding studies suggested mono-dentate binding of thiadiazole, oxadiazole, and triazole rings to the active site dicopper center of tyrosinase including hydrophobicity contributing to the potent inhibition. Kinetic plots showed mixed-type of inhibition by all 25 compounds. Substitutions at C3 of the triazole ring and C5 of the thiadiazole/oxadiazole rings were found to be playing a major role in the high binding affinity to tyrosinase. The current work may help develop new potent tyrosinase inhibitors against hyperpigmentation including potential insecticides.

Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues

Twenty-one hydrazides were synthesized by treating different esters with hydrazine hydrate. Substituted hydrazides were obtained by treating hydrazides with alkyl/aryl/acyl halides. Some of these compounds exhibit potential in vitro leishmanicidal activity. The structures of all the synthesized compounds were confirmed by spectroscopic analysis.

Synthesis and biological screening of 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles and of their intermediates

To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates 1 and 2 were substituted with p-toluenesulfonyl (→ 4 and 5), benzoyl (→ 6 and 7), and benzyl groups (→ 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12, 24, 28, and 29 appreciable antifungal activities. Compound 7 inhibits α-chymotrypsin.