156732-13-7

Basic information

• Product Name: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one
• Synonyms: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one;(S,Z)-5-AMINO-2-(DIBENZYLAMINO)-1,6-DIPHENYLHEX-4-EN-3-ONE,98%;(S,Z)-5-AMino-2-(dibenzylaMino)-1,6-diphenylhex-4-ene-3-one (DAH-II);(2S)-5-AMino-2-[bis(phenylMethyl)aMino]-1,6-diphenyl-4-hexen-3-one;(S)-2-AMino-5-(N,N-dibenzylaMino)-4-oxo-1,6-diphenylhex-2-ene;(S,Z)-5-AMino-2-(DibenzylaMino)-1,6-Diphenylhex-4-En-3-One (DAH-2);2-AMINO-5(S)-N,N-DIBENZYL AMINO-3-OXO-1,6-DIPHENYL HEX-2-ENE;4-Hexen-3-one,5-aMino-2-[bis(phenylMethyl)aMino]-1,6-diphenyl-, (2S)-
• CAS NO: 156732-13-7
• Molecular Formula: C32H32N2O
• Molecular Weight: 460.61
• EINECS: 1312995-182-4
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates
• Mol File: 156732-13-7.mol

Chemical Properties

• Boiling Point: 626.161 °C at 760 mmHg
• Flash Point: 332.49 °C
• Appearance: /
• Density: 1.137 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• PKA: 5.58±0.70(Predicted)
• CAS DataBase Reference: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(156732-13-7)
• EPA Substance Registry System: (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one(156732-13-7)

Safety Data

• Hazardous Substances Data: 156732-13-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one is used as a chemical intermediate for the production of Ritonavir, an antiretroviral drug. Its role in the synthesis process is crucial for the development of medications that help combat HIV and AIDS, providing a vital contribution to the healthcare sector.
Used in Chemical Synthesis:
As a light yellow crystalline solid, (S,Z)-5-Amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one can also be utilized in various chemical synthesis processes, potentially leading to the creation of other valuable compounds and materials. Its unique structure and properties make it a versatile building block in the field of organic chemistry.

InChI:InChI=1/C32H32N2O/c33-30(21-26-13-5-1-6-14-26)23-32(35)31(22-27-15-7-2-8-16-27)34(24-28-17-9-3-10-18-28)25-29-19-11-4-12-20-29/h1-20,23,31H,21-22,24-25,33H2/b30-23-/t31-/m0/s1

Upstream product

• 156732-12-6 (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 75-05-8 acetonitrile 
• 63-91-2 L-phenylalanine 
• 100-44-7 benzyl chloride 

Downstream Products

• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 
• 156732-14-8 (2S,5S)-5-amino-2-dibenzylamino-3-oxo-1,6-diphenylhexane 
• 162849-93-6 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 192725-49-8 (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane 

Relevant articles and documents

A convenient synthesis of enaminones using tandem acetonitrile condensation Grignard addition

Condensations of N,N-dibenzyl α-amino esters with the anion of acetonitrile followed by the addition of a Grignard reagent(proceed in excellent yields. This affords rapid access to the peptidomimetic precursor α-amino enaminones in one pot one the esters.

Structural Analysis of Potent Hybrid HIV-1 Protease Inhibitors Containing Bis-tetrahydrofuran in a Pseudosymmetric Dipeptide Isostere

The design, synthesis, and X-ray structural analysis of hybrid HIV-1 protease inhibitors (PIs) containing bis-tetrahydrofuran (bis-THF) in a pseudo-C2-symmetric dipeptide isostere are described. A series of PIs were synthesized by incorporating bis-THF of darunavir on either side of the Phe-Phe isostere of lopinavir in combination with hydrophobic amino acids on the opposite P2/P2′ position. Structure-activity relationship studies indicated that the bis-THF moiety can be attached at either the P2 or P2′ position without significantly affecting potency. However, the group on the opposite P2/P2′ position had a dramatic effect on potency depending on the size and shape of the side chain. Cocrystal structures of inhibitors with wild-type HIV-1 protease revealed that the bis-THF moiety retained similar interactions as observed in the darunavir-protease complex regardless of the position on the Phe-Phe isostere. Analyses of cocrystal structures and molecular dynamics simulations provide insights into optimizing HIV-1 PIs containing bis-THF in non-sulfonamide dipeptide isosteres.

Preparation method of ritonavir and lopinavir intermediates

The invention discloses a preparation method of ritonavir and lopinavir intermediates. The method comprises the steps: using L-phenylalanine as a raw material to react with benzyl chloride in potassium carbonate and an alkaline aqueous solution to obtain N, N-dimethylformamide; condensing with acetonitrile under the action of sodium amide; carrying out addition reaction with benzyl magnesium chloride; sequentially reducing enamine and carbonyl by using sodium borohydride/methanesulfonic acid and sodium borohydride/trifluoroacetic acid reagents; obtaining a stereoselective product, namely, dibenzylamino-3-hydroxy-5-amino-1, 2, 4-triazole under the induction effect of a chiral inducer; the stereoselective product reacts with di-tert-butyl methyl dicarbonate in a potassium carbonate/tetrahydrofuran solution, ammonium formate and palladium/carbon are used for reduction debenzylation, and the intermediate BDH is obtained. The preparation method is high in stereoselectivity, the diastereomeric excess (de%) value of the chiral product is high, the reaction steps are short, the product yield is high and generated three wastes are few.

Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration

Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.

Method for synthesizing ritonavir intermediate

The invention relates to a method for synthesizing a ritonavir intermediate. The intermediate is (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. The method comprises the following steps: mixing L-phenylalanine, water and sodium hydroxide, adding benzyl chloride, adding heptane, washing the above obtained material with a methanol-water solution, and carrying out reduced pressure evaporation to obtain yellow oil benzyl 2-dibenzylamino-3-phenylpropionate; and dissolving the yellow oil in methyl tert-butyl ether under the protection of nitrogen, reacting the obtained solution with anhydrous acetonitrile, adding sodium hydride, stirring all above materials, slowly dropwise adding a Grignard reagent, cooling, adding anhydrous methanol for hydrolyzing superfluous sodium amide, allowing the obtained solution to stand for layering, extracting the obtained water layer with methyl tert-butyl ether, mixing oil layers, concentrating the obtained oil layer mixture, evaporating the obtained concentrate to obtain oil, adding anhydrous methanol, filtering the oil, and carrying out vacuum drying to obtain white powder which is the ritonavir intermediate (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. Compared with traditional technologies, the method provided by the invention has the advantages of reaction step simplification, reaction cost reduction, and reduction of use of toxic reagents.

Synthesis of (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one

L-Phenylalanine taken as a starting material is protected with benzyl chloride and procedure simplified by not charging with ethyl alcohol. Subsequently with the further simplification of skipping the atmospheric distillation of MTBE (methyl tert-butyl ether), (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one, the significant intermediate of Ritonavir and Lopinavir, is obtained from cyanidation, Grignard reaction and reduction.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

Novel Lopinavir analogues incorporating non-Aromatic P-1 side chains - Synthesis and structure-activity relationships

The HIV protease inhibitor Lopinavir has a pseudosymmetric core unit incorporating benzyl groups at both P-1, P-1′ positions. A series of analogues incorporating non-aromatic side chains at the P-1 position were synthesized and the structure-activity relationships explored.

Process for the preparation of substituted keto-enamines

The present invention discloses a process for the preparation of a compound having formula 4: STR1 The process comprises the step of reacting an enolate having the formula: STR2 with a Grignard reagent. The enolate salt is formed in situ from the reaction of a protected ester wherein M is an alkali metal. R6 and R7 are each hydrogen or are independently selected from STR3 wherein Ra and Rb are independently selected from hydrogen, lower alkyl and phenyl and Rc, Rd and Re are independently selected from hydrogen, lower alkyl, trifluoromethyl, alkoxy, halo and phenyl; and STR4 wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from lower alkyl, trifluoromethyl, alkoxy and halo. Alternatively, R6 is as defined above and R7 is R12 OC(O)-- wherein R12 is benzyl; or R6 and R7 taken together with the nitrogen atom to which they are bonded form STR5 wherein Rf, Rg, Rh and Ri are independently selected from hydrogen, lower alkyl, alkoxy, halogen and trifluoromethyl.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.