822519-90-4

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine is used as a potential antifungal and antibacterial agent due to its ability to target and inhibit the growth of various fungi and bacteria. Its unique structure and stereochemistry contribute to its effectiveness in this application.
Used in Cancer Treatment Research:
(1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine is used as a candidate for cancer treatment, as it has shown potential in inhibiting the growth and proliferation of cancer cells. Further research is needed to understand its mechanisms of action and to develop it into a viable therapeutic agent for cancer patients.

Upstream product

• 45709-05-5 4-chlorobenzylideneimine 
• 104-88-1 4-chlorobenzaldehyde 
• 820231-56-9 C₂₂H₃₀Cl₂N₂O₂S₂ 
• 1207946-36-8 (S)-N-(4-chlorobenzylidene)-2-methylpropane-2-sulfinamide 
• 144406-59-7 (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-methyl-butyric acid 3-((S)-2-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-3-methyl-butyryloxy)-propyl ester 
• 169532-37-0 (3S,5R,6R,8S)-5,6-Bis-(4-chloro-phenyl)-3,8-diisopropyl-1,10-dioxa-4,7-diaza-cyclotridecane-2,9-dione 

Downstream Products

• 144406-65-5 [(1R,2R)-2-Benzyloxycarbonylamino-1,2-bis-(4-chloro-phenyl)-ethyl]-carbamic acid benzyl ester 
• 503112-11-6 (4S,5S)-2-(2-iodophenyl)-4,5-bis-(4-chlorophenyl)-4,5-dihydro-1H-imidazole 
• 503112-31-0 (S,S)-iodo-N-2-naphthoyl-bis-(4-chlorophenyl) imidazoline 

Relevant academic research and scientific papers

Diboron glycol ester as well as preparation method, intermediate and application thereof

The invention discloses diboron glycol ester as well as a preparation method, an intermediate and application thereof. The diboron glycol ester can be used for inducing reductive coupling reaction with imine as a substrate, and the substrate can be obtained by reaction of aldehyde and ammonia and is very easy to obtain and quite low in cost. The product can be separated from a reaction system onlyby acid-base operation without column chromatography purification, and the post-treatment mode is convenient and easy to operate. The yield of the obtained product is high, and protective group operation is not needed. The diboron glycol ester has chirality, the stereoselectivity of the reductive coupling reaction is generally excellent, and 99% ee chiral diamine can be obtained only through simple recrystallization. The diboron glycol ester can be obtained by reacting diol with diboron glycol ester, the diol is convenient to prepare and easy to amplify, the diol can be recycled from a reaction solution through simple acid-base operation, the recovery rate reaches 95%, and the preparation cost is further saved.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Synthesis and cytotoxic evaluation of novel platinum(II) complexes with C2-asymmetric and C2-symmetric chiral vicinal diamines

A series of new platinum(II) complexes with C2-asymmetric and C2-symmetric 1,2-diamines were designed and synthesized by convenient methods, involving samarium diiodide induced reductive coupling as the key step. The results of cytotoxicity showed that compounds (R,R)-11a and (S,S)-11a, two novel platinum(II) complexes with asymmetric 1,2-diamines, exhibited more potent cytotoxicity than that of oxaliplatin against all leukemia cell lines. Interestingly, (R,R)-11a and (S,S)-11a demonstrated less potent activity against three solid cancer cell lines than that of oxaliplatin, which indicated that these two compounds may only selectively inhibit the leukemia cell lines. In contrast, (R,R)-15a and (S,S)-15a, two platinum(II) complexes with symmetric 1,2-diamines, showed similar cytotoxicity to that of oxaliplatin against all leukemia cell lines and more potent activity against solid cancer cell lines. Further flow cytometry data indicated that (R,R)-11a could obviously arrest leukemia K562 cells in G2/M phases. A series of new platinum(II) complexes with C2-asymmetric and C2-symmetric 1,2-diamines were designed and synthesized by convenient methods, involving samarium diiodide induced reductive coupling as the key step. The cytotoxicity of these analogs against four leukemia and three solid cancer cell lines was evaluated and the preliminary structure-activity relationship is also discussed. Flow cytometry data indicated that (R,R)-11a could obviously arrest leukemia K562 cells in G2/M phases. Copyright

Synthesis of Nitrogen-Containing Macrocycles with Reductive Intramolecular Coupling of Aromatic Diimines

Reductive intramolecular coupling of aromatic diimines is an effective method for the synthesis of a variety of nitrogen-containing macrocycles. 1,4-Diazacrown ethers 3 were effectively synthesized by intramolecular coupling of bis(imino ethers) 9 promoted by electroreduction (method A) or chemical reduction with zinc powder (method B) in the presence of methanesulfonic acid.In spite of the formation of macrocycles, the yields of 3 were relatively high.This can be explained by the formation of proton-bridged intermediates 14, in which intramolecular hydrogen bonds are formed between hydrogen and oxygen atoms of diiminium salts.Method B was more effective in the formation of 1,4-diaza-12-crown-4 derivatives 3 (n = 1) due to the template effect of Zn(2+).Optically active macrocyclic bislactones 4 were synthesized stereoselectively by reductive intramolecular coupling of bis(imino esters) 20 with zinc powder (method B).The high stereoselectivity is explained by considering proton-bridged intermediate 23.The resultant compounds 4 were transformed to optically active 1,2-diarylethylenediamines 7.Various sizes of macrocyclic bislactams 5 were synthesized by reductive intramolecular coupling of bis(imino amides) 26 with zinc powder (method B).Reduction of 5 gave the corresponding macrocyclic polyamines 6.

A novel method for stereoselective synthesis of (1R,2R)-diarylethylenediamines by reductive intramolecular coupling of aromatic diimines

Reduction with zinc has been found to be an effective method for selective synthesis of (1R,2R)-diarylethylenediamines from the corresponding chiral aromatic diimines through their intramolecular coupling.