2443-66-5

Usage

Uses

Used in Pharmaceutical Synthesis:
MANDELIC ACID HYDRAZIDE is used as a reducing agent for the synthesis of pharmaceuticals and organic compounds, facilitating the production of chiral drugs and various pharmaceutical intermediates.
Used in Antimicrobial Applications:
In the field of microbiology, MANDELIC ACID HYDRAZIDE is used as an antimicrobial agent to inhibit the growth of bacteria and fungi, showcasing its potential in combating microbial infections.
Used in Antioxidant Formulations:
Given its antioxidant properties, MANDELIC ACID HYDRAZIDE is used in the development of antioxidant formulations, which can help protect against oxidative stress and related cellular damage.
Used in Chemical Industry:
In the chemical industry, MANDELIC ACID HYDRAZIDE is utilized as a precursor in the synthesis of various organic compounds, contributing to the creation of a wide range of chemical products.

InChI:InChI=1/C8H10N2O2/c9-10-8(12)7(11)6-4-2-1-3-5-6/h1-5,7,11H,9H2,(H,10,12)/t7-/m1/s1

Upstream product

• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 4358-87-6 (RS)-methyl mandelate 

Downstream Products

• 109502-62-7 N-hippuroyl-N'-mandeloyl-hydrazine 
• 626-36-8 ethyl allophanate 
• 70753-21-8 mandelic acid-benzylidenehydrazide 
• 91181-11-2 mandelic acid-isopropylidenehydrazide 
• 98750-10-8 α-hydroxy-N-(2-oxo-2-phenylethylidene)phenylacetohydrazide 
• 122432-94-4 Hydroxy-phenyl-acetic acid [1-(2-chloro-phenyl)-eth-(E)-ylidene]-hydrazide 
• 177337-28-9 Hydroxy-phenyl-acetic acid [1-(2-chloro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 42596-23-6 Hydroxy-phenyl-acetic acid [1-(2,6-dichloro-phenyl)-meth-(E)-ylidene]-hydrazide 
• 4358-87-6 (RS)-methyl mandelate 
• 1239611-00-7 4-(4-fluorophenyl)-5-[hydroxy(phenyl)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 642075-27-2 4-benzyl-5-[hydroxy(phenyl)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 

Relevant academic research and scientific papers

Preparation and Thermolysis of N-Ammonioamidates Containing Hydroxyl Group in Acyl Moiety

The title ammonioamidates (aminimides) were prepared in satisfactory yields from lactones or α-hydroxy carboxylates.By the thermolysis of these aminimides in mesitylene, some types of urethane compounds were formed, depending on the structure of the aminimide and on the concentration of the solutions.

Novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group acting as human carbonic anhydrase IX inhibitors

A small collection of 26 structurally novel thiazolidinone-containing compounds, without the well-known sulphonamide zinc-binding group, were synthesised and tested in enzyme inhibition assays against the tumour-associated hCA IX enzyme. Inhibition constants in the lower micromolar region (KI I values are relatively weak, the fact that they do not contain a sulphonamide moiety suggests that these compounds do not interact with the active site zinc ion. Therefore, docking studies and molecular dynamics simulations have been performed to suggest binding poses for these structurally novel inhibitors.

Design, synthesis and antifungal evaluation of novel mandelic acid derivatives containing a 1,3,4-oxadiazothioether moiety

A series of novel mandelic acid derivatives containing a 1,3,4-oxadiazothioether moiety were designed and synthesized. Bioassay results showed that some target compounds exhibited certain antifungal activity against six kinds of pathogenic fungi in vitro. Among the compounds, the EC50 values of T41 against Gibberella saubinetii, Verticillium dahlia and Sclerotinia sclerotiorum were 31.0, 27.0 and 32.1?μg/ml, respectively, and the EC50 value of T14 against S. sclerotiorum was 14.7?μg/ml. The antifungal activity against the resistant fungus S. sclerotiorum indicated that this series of target compounds may have the similar action modes or sites as the commercialized succinate dehydrogenase inhibitor carboxin. A morphological study with fluorescence microscope demonstrated that T41 can significantly destroy the membrane integrity of G. saubinetii.

Benzophenone compound containing 1,thiadiazole thioether structure and application thereof

The invention discloses a benzophenone compound containing 1,thiadiazole thioether structure, its characterized in that: its structural formula is as follows: Herein R is an alkyl group. Benzyl or substituted benzyl. The invention is based on the structure of mandelic acid derivatives containing '1,oxadiazole thioether'. The 'hydroxyl group' in the compound structure is replaced by '1,thiadiazole thioether', and a series of benzophenone compounds containing 1,thiadiazole thioether structures has been synthesized, and the compound has good bacteriostatic activity on various plant pathogenic bacteria. Compared with a high-activity compound reported in early-stage work of a title group, the compound has a novel 'ketone' structure, shows certain bacteriostatic activity, and provides an important scientific basis for research and development and creation of new pesticides.

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.

Dithiocarbamate as a valuable scaffold for the inhibition of metallo-β-lactmases

The ‘superbug’ infection caused by metallo-β-lactamases (MβLs) has grown into an emergent health threat. Given the clinical importance of MβLs, a novel scaffold, dithiocarbamate, was constructed. The obtained molecules, DC1, DC8 and DC10, inhibited MβLs NDM-1, VIM-2, IMP-1, ImiS and L1 from all three subclasses, exhibiting an IC50 50 0.22 μM). DC1-2, DC4, DC8 and DC10 restored antimicrobial effects of cefazolin and imipenem against E. coli-BL21, producing NDM-1, ImiS or L1, and DC1 showed the best inhibition of E. coli cells, expressing the three MβLs, resulting in a 2-16-fold reduction in the minimum inhibitory concentrations (MICs) of both antibiotics. Kinetics and isothermal titration calorimetry (ITC) assays showed that DC1 exhibited a reversible, and partially mixed inhibition, of NDM-1, ImiS and L1, with Ki values of 0.29, 0.14 and 5.06 μM, respectively. Docking studies suggest that the hydroxyl and carbonyl groups of DC1 form coordinate bonds with the Zn (II) ions, in the active center of NDM-1, ImiS and L1, thereby inhibiting the activity of the enzymes. Cytotoxicity assays showed that DC1, DC3, DC7 and DC9 have low toxicity in L929 mouse fibroblastic cells, at a dose of up to 250 μM. These studies revealed that the dithiocarbamate is a valuable scaffold for the development of MβLs inhibitors.

Multiple Hydrogen Bonds Promoted ESIPT and AIE-active Chiral Salicylaldehyde Hydrazide

The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules (41 samples) have been designed and prepared. Even though these soft materials contain a very small π-conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited-state intramolecular proton-transfer (ESIPT) to display strong blue, green, yellow, and orange aggregation-induced emission (AIE) with large Stokes shifts (up to 184 nm) and high fluorescence quantum yields (Ф up to 0.20). Unusual mechanochromic fluorescence enhancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2+ (Ф up to 0.46) probes, universal anion (Ф up to 0.14) and unprotected amino acids (Ф up to 0.16) probes, and chiral diamine (enantiomeric selectivity and Ф up to 0.36 and 0.062, respectively) receptors. Combining their advantages of AIE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AIE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple-stimuli-responsive smart materials.

A containing "1, 3, 4 - oxadiazole thioether" mandelic acid derivatives and use thereof

The invention discloses a containing "1, 3, 4 - oxadiazole thioether" mandelic acid derivatives and their use in the application of the fungi anti-plants sickness, the compound has the general formula (B) structure shown: In the formula, R1 Is H, methyl, fluorine or chlorine, R2 C for containing1 - 3 Straight-chain alkyl, containing C1 - 4 Branched alkyl, propenyl, propynyl or mono-substituted benzyl, wherein the single substituted benzyl substituent is "nitro, methyl, trifluoromethyl, methoxy, three methoxy, fluorine, and bromine". The invention to replace the mandelic acid as the skeleton, mandelic acid introduced in the structure of the "oxadiazole thioether" structure, design synthesizing a containing "1, 3, 4 - oxadiazole thioether" structure of the mandelic acid derivatives, anti-plant disease fungal activity tests show that the class of compounds of plant diseases caused by fungi has good inhibition activity, for the new pesticide research and development and create provide important scientific basis.

Synthesis, characterization, antimycobacterial and anticancer evaluation of new 1,2,4-triazole derivatives

A series of 4,5-disubstituted-1,2,4-triazole-3-thione derivatives (4a-e) and their N-Mannich bases (5a-e), together with a S-benzyl derivative (6), were synthesized and evaluated as antimycobacterial and antiproliferative agents. The structures of the compounds were established by IR, 1H-NMR, 13C-NMR and 2D-NMR spectroscopic methods and microanalysis. 4 and 5 were screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Three of the tested compounds (4d, 4e and 5e) were found to be active in the primary screen. Among them, compound 4e was the most potent one with IC90 and IC50 values of 27.5 and 20.8 μg/mL, respectively. Additionally, compounds 4b, 4c, 5b, 5c, 5e and 6 were subjected to the NCI's in vitro disease-oriented antitumor screening to be evaluated for antitumor activity at a single dose of 10 μM. The S-benzyl derivative 6 exhibited promising antiproliferative activity against leukemia CCRF-CEM, RPMI-8226 and SR, non-small cell lung cancer HOP-92, melanoma UACC-62 and renal cancer UO-31 cell lines.

Antihypertensive actions of hydrazidones: Study of acylated dichloroarylhydrazones

A series of acylated dichloroarylhydrazones has been prepared and evaluated on spontaneously hypertensive rats (SHR). The presence of 2-Cl and 6-Cl aromatic substituents in a clonidine like position is not required since derivatives bearing 2- and 4-chloro as well as 3- and 4-chloro substituents exert antihypertensive activities. Activity is also maintained in certain 2,6 disubstituted derivatives where one of the chlorine atoms is replaced by F or NO2.