1871-76-7

Usage

Uses

1. Used in Pharmaceutical Industry:
Diphenylacetyl chloride is used as a reagent for the synthesis of β-lactam estrogen receptor antagonists, which promote antiproliferative and anti-tubulin polymerization activity. This application is significant in the development of potential treatments for hormone-dependent cancers and other related conditions.
2. Used in Chemical Synthesis:
Diphenylacetyl chloride is utilized as a reagent in the regioselective acylation of cyclomalto-oligosaccharides, a process that is crucial for the production of specific chemical compounds with desired properties.
3. Used in Local Anesthetics:
Diphenylacetyl chloride is employed in the preparation of N-substituted amides, which possess local anesthetic properties. These compounds are essential in the development of anesthetic drugs used in medical procedures to provide pain relief during surgeries and other interventions.

InChI:InChI=1/C14H11ClO/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H

Upstream product

• 117-34-0 2,2-diphenylacetic acid 
• 543-20-4 succinoyl dichloride 
• 525-06-4 diphenyl ketene 
• 121342-36-7 2-anilino-2-oxoacetyl chloride 
• 75-36-5 acetyl chloride 
• 2040-76-8 phenylcarbamic acid chloride 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 
• 76-93-7 Benzilic acid 
• 79-37-8 oxalyl dichloride 
• 5350-81-2 Diphenylessiggsaeure-tert-butylester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 3469-00-9 methyl 2,2-diphenylacetate 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 60678-46-8 N-(2,2-diphenylacetyl)pyrrolidine 
• 13294-63-8 3-chloro-1,1-diphenyl-acetone 
• 33609-25-5 3-bromo-1,1-diphenylpropan-2-one 
• 32640-78-1 3-diazo-1,1-diphenyl-2-propanone 
• 4107-00-0 2,2-diphenyl-1-(piperidin-1-yl)ethanone 
• 56230-67-2 1-diphenylacetyl-4-methyl-piperazine 
• 102171-66-4 diphenyl-acetic acid tetrahydrothiopyran-4-yl ester 
• 5411-36-9 diphenyl-thioacetic acid S-(2-pyrrolidino-ethyl ester); hydrochloride 
• 37963-15-8 diphenylacetic acid-(1-methyl-[3]piperidyl ester) 
• 97762-23-7 4-diphenyl acetoxy N-methyl piperidine 
• 641-61-2 diphenyl-acetic acid-(2-dibutylamino-ethyl ester) 
• 127158-39-8 diphenyl-acetic acid-(3-pyrrolidino-propyl ester) 
• 3626-07-1 diphenyl-acetic acid-(2-piperidino-ethyl ester) 
• 10120-30-6 diphenyl-acetic acid-(2-piperidino-ethylamide) 

Relevant academic research and scientific papers

Transient Kinetics and Quantum Yield Studies of Nanocrystalline α-Phenyl-Substituted Ketones: Sorting Out Reactions from Singlet and Triplet Excited States

Recent work has shown that diarylmethyl radicals generated by pulsed laser excitation in nanocrystalline (NC) suspensions of tetraarylacetones constitute a valuable probe for the detailed mechanistic analysis of the solid-state photodecarbonylation reaction. Using a combination of reaction quantum yields and laser flash photolysis in nanocrystalline suspensions of ketones with different substituents on one of the α-carbons, we are able to suggest with confidence that a significant fraction of the initial α-cleavage reaction takes place from the ketone singlet excited state, that the originally formed diarylmethyl-acyl radical pair loses CO in the crystal with time constants in the sub-nanosecond regime, and that the secondary bis(diarylmethyl) triplet radical pair has a lifetime limited by the rate of intersystem crossing of ca. 70 ns.

Ruthenium-catalysed one-pot regio- and diastereoselective synthesis of pyrrolo[1,2-a] indoles via cascade C-H functionalization/annulation

A cascade approach has been developed towards dual C-C bond formation via consecutive C-H functionalization/cyclization giving access to pyrrolo[1,2-a]indoles in a highly regio- and diastereoselective manner using catalytic [Ru(p-cymene)Cl2]2. The methodology was further expanded to attain pentacyclic structures involving manifold C-C bond creation.

Pharmacological studies and synthesis of morpholino alkyl derivatives

Seven morpholin derivatives were synthesized (compounds 1-7) and their behavioural effects were evaluated; the elements considered were locomotor activity, motor coordination, catalepsy, stereotyped behaviour and antinociception. All the compounds, at doses of 10-20-40 mg/kg/i.p., induced a reduction of all behavioural elements without a significant antinociceptive effect. These results indicate that these morpholin derivatives affect the central nervous system.

Triphenylacetic acid amides: Molecular propellers with induced chirality

The combination of electronic circular dichroism spectroscopy (ECD), X-ray diffraction, and theoretical calculations permitted a detailed description of an unexpected chirality transfer in triphenylacetamides, which is achieved solely through weak intramolecular interactions. The observed phenomenon proceeds as a cascade process. The triphenylacetamide chromophore is sensitive to even small changes in the relative size of the substituent attached to the stereogenic center. Substitution at the stereogenic center influences helicity of the distal trityl chromophore but does not affect its propeller shape. Deformation of the propeller shape and consequent loss of its C3 symmetry results mainly from substitution of the amide hydrogen and is connected with an increase in steric hindrance. As an outcome of our studies, a model of optical activity of chiral triphenylacetamides is proposed. The performed X-ray studies revealed that this novel class of chiral compounds is likely to be of additional value due to the porosity of the crystals.

RECEPTOR INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING SAME, AND USE THEREOF

The present invention discloses a receptor inhibitor of formula (I), a pharmaceutical composition comprising the same and the use thereof.

Design and synthesis of novel N-[3-(benzimidazol-2-ylamino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives as potential anticancer agents

In this contribution, we report the design, synthesis and cytotoxicity studies of a series of N-[3-(benzimidazol-2-yl-amino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives. In vitro cytotoxicity assay of 26 selected compounds was carried out at National Cancer Institute (NCI), USA. Out of them, compounds 10e (NSC D-762842/1) and 11s (NSC D-764942/1) have shown remarkable cytotoxicity with GI50 values ranging between “0.589–14.3?μM” and “0.276–12.3?μM,” respectively, in the representative nine subpanels of human tumor cell lines. Further, flow cytometry analysis demonstrated that compound 10e exerted cell cycle arrest at G2/M phase and showed dose-dependent enhancement in apoptosis in K-562 leukemia cancer cells.

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation

AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is