74641-30-8

Usage

Uses

Used in Pharmaceutical Industry:
meso-1,2-Bis(4-chlorophenyl)ethylenediamine is used as a reactant in the synthesis of sinomenine derivatives, which are known for their potent TNF-α inhibitory activity. TNF-α (tumor necrosis factor-alpha) is a cytokine involved in systemic inflammation and is implicated in various inflammatory and autoimmune diseases. By inhibiting TNF-α, sinomenine derivatives can potentially be used for the treatment of such conditions.
In the synthesis process, meso-1,2-Bis(4-chlorophenyl)ethylenediamine plays a crucial role in the formation of the desired sinomenine derivatives, contributing to their biological activity and therapeutic potential. Its unique structure allows for the creation of compounds with specific binding affinities and selectivity, which can be further optimized for improved efficacy and safety in pharmaceutical applications.

InChI:InChI=1/C14H14Cl2N2/c15-11-5-1-9(2-6-11)13(17)14(18)10-3-7-12(16)8-4-10/h1-8,13-14H,17-18H2/p+2/t13-,14+

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 3848-36-0 4-chlorobenzaldoxime 
• 41097-37-4 (1E, 2E)-1,2-bis (4-chlorobenzylidene) hydrazine 
• 115294-32-1 4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide] 

Downstream Products

• 86212-33-1 4,5-di(p-chlorophenyl)imidazoline-2-thione 
• 944253-11-6 meso-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-pyridin-3-yl)-4,5-dihydro-1H-imidazole 

Relevant academic research and scientific papers

MDM2 DEGRADERS AND USES THEREOF

The present invention relates to compounds and methods useful for the modulation of mouse double minute 2 homolog ("MDM2") protein via ubiquitination and/or degradation by compounds according to the present invention.

Dimer ester micromolecule PROTACs for inducing MDM2 to self-degrade E3 ubiquitin ligase

The invention provides dimer ester micromolecule PROTACs for inducing MDM2 to self-degrade E3 ubiquitin ligase. The structure of the PROTACs is shown in the specification, wherein in a compound (I), L1 is C1-C30 linear or branched alkyl with or without a substituent group, and any carbon atom in L1 is optionally replaced by heteroatom; R1, R2, R3 and R4 are C1-C30 linear or branched alkyl with orwithout a substituent group, C1-C30 aryl with or a without substituent group, C1-C30 linear or branched alkylaryl with or without a substituent group or C1-C30 linear or branched aryl alkyl with or without a substituent group respectively and independently; X1, X2, X3 and X4 are halogen respectively and independently.

Chiral synthesis method for producing cis-imidazoline compounds for pharmaceutical use

This invention provides a method for enantioselective synthesis of cis-imidazolines and related structures through chiral resolution. A chiral acid is used to separate enantiomeric precursors of the cis-imidazolines from a racemic mixture by selective cry

Small Molecules Simultaneously Inhibiting p53-Murine Double Minute 2 (MDM2) Interaction and Histone Deacetylases (HDACs): Discovery of Novel Multitargeting Antitumor Agents

p53-Murine double minute 2 (MDM2) interaction and histone deacetylases (HDACs) are important targets in antitumor drug development. Inspired by the synergistic effects between MDM2 and HDACs, the first MDM2/HDACs dual inhibitors were identified, which sho

Dimer amide micromolecule PROTACs for inducing MDM2 to self-degrade E3 ubiquitin ligase

The invention provides dimer amide micromolecule PROTACs for inducing MDM2 to self-degrade E3 ubiquitin ligase. The structure of the PROTACs is shown in the specification, wherein in a compound (I), L1 is C1-C30 linear or branched alkyl with or without a substituent group, and any carbon atom in L1 is optionally replaced by heteroatom; R1, R2, R3 and R4 are C1-C30 linear or branched alkyl with orwithout a substituent group, C1-C30 aryl with or without a substituent group, C1-C30 linear or branched alkylaryl with or without a substituent group or C1-C30 linear or branched aryl alkyl with or without a substituent group respectively and independently; X1, X2, X3 and X4 are halogen respectively and independently.

Lipase-catalyzed desymmetrization of meso-1,2-diaryl-1,2-diaminoethanes

The synthesis and enzyme-catalyzed desymmetrization of meso-1,2-diaryl-1,2- diaminoethanes have been investigated. A family of aromatic meso-1,2-diamines, containing different substitution patterns in the aromatic ring, was first prepared and then desymmetrized enantioselectively using lipases as biocatalysts. Selective alkoxycarbonylation of one of the amino groups was achieved using allyl carbonates, isolating the corresponding allyl monocarbamates with moderate to high enantiomeric excess at 45 C. Candida antarctica lipase types A (CAL-A) and B (CAL-B) displayed the best activities and stereopreferences, with a dramatic influence being observed depending on the diamine structure. Non substituted and para-substituted aryldiamines led to the formation of allyl carbamates with good enantiomeric excess, using CAL-A for the less hindered substrates and CAL-B for the more hindered ones. On the other hand meta- and ortho-derivatives afforded low or negligible conversions and selectivities, respectively.

Design, synthesis and CoMFA studies of N1-amino acid substituted 2,4,5-triphenyl imidazoline derivatives as p53-MDM2 binding inhibitors

A series of novel N1-amino-acid substituted 2,4,5-triphenyl imidazoline derivatives was designed and synthesized based on our previous studies. All synthesized target compounds were screened for their p53-MDM2 binding inhibitory activities and anti-proliferative activities against five cancer cell lines. Among them, twelve compounds displayed improved binding inhibitory activities and most compounds showed higher cell growth inhibition activities with IC 50 values in the low micromolar range. Compound 6c exhibited marked p53-MDM2 binding inhibitory activity (IC50 = 0.59 μM) which was eightfold more potent than that of Nutlin-1 (IC50 = 4.78 μM). CoMFA analysis was performed based on obtained biological data and resulted in a statistically significant CoMFA model with high predict abilities (q 2 = 0.645, r2 = 0.979).

Design, synthesis, and biological evaluation of imidazoline derivatives as p53-MDM2 binding inhibitors

Three series of novel imidazoline derivatives were designed, synthesized, and evaluated for their p53-MDM2 binding inhibitory activities, and anti-proliferation activities against PC3, A549, KB, and HCT116 cancer cell lines. Five of the tested compounds showed enhanced p53-MDM2 binding inhibitory potency and anti-proliferation activities in comparison with that of Nutlin-1. Flow cytometric analysis indicated that compound 7c, one of the most potent p53-MDM2 binding inhibitors with a Ki value of 0.6 μM, showed its ability to arrest cell cycle progression.

Substituted Dihydroimidazoles and their Use in the Treatment of Tumors

The invention relates to dihydroimidazoles of formula rac-(I), wherein the radicals and symbols are as defined herein; their use as inhibitors of the interaction of the MDM2 protein with a p53-like peptide, new pharmaceutical formulations comprising said compounds, said compounds for use in the therapeutic treatment of warm-blooded animals, especially humans, their use in the treatment of proliferative diseases or for the manufacture of pharmaceutical formulations useful in the treatment of proliferative diseases that respond to modulation of the interaction of the MDM2 protein with a p53-like peptide, a pharmaceutical formulation e.g. useful in the treatment of proliferative diseases that respond to modulation of the interaction of the MDM2 protein with a p53-like peptide comprising said compound, methods of treatment comprising administration of said compounds to a warm-blooded animal, and/or processes for the manufacture of said compounds.

Reductive coupling of aromatic oxims and azines to 1,2-diamines using Zn-MsOH or Zn-TiCl4

The reduction of aromatic aldoxims and azines with Zn in the presence of MsOH or TiCl4 afforded N,N′-unsubstituted 1,2-diamines in one-step. The reductive coupling with Zn-MsOH gave meso 1,2-diamines selectively, whereas dl 1,2-diamines were fo