149950-60-7

Basic information

• Product Name: emivirine
• Synonyms: emivirine;6-benzyl-1-(ethoxymethyl)-5-isopropyluracil;MKC 442
• CAS NO: 149950-60-7
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.41
• Mol File: 149950-60-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.133g/cm³
• Refractive Index: 1.542
• CAS DataBase Reference: emivirine(CAS DataBase Reference)
• NIST Chemistry Reference: emivirine(149950-60-7)
• EPA Substance Registry System: emivirine(149950-60-7)

Safety Data

• Hazardous Substances Data: 149950-60-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Emivirine is used as an antiviral agent for the treatment of HIV-1 infections. It acts as a non-nucleoside reverse transcriptase inhibitor, preventing the replication of the virus and thus helping to manage the infection in patients.
Used in COVID-19 Treatment:
Emivirine has also been identified as a potential treatment option for diseases caused by SARS-CoV-2, the virus responsible for COVID-19. Its antiviral properties make it a candidate for further research and development in this area.
Brand Name:
Emivirine is marketed under the brand name Coactinon by Mitsubishi Chemical Corporation in Japan.

Hazard

Moderately toxic by ingestion.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)

Upstream product

• 1020069-04-8 4-benzyl-5-isopropyl-2,6-bis-trimethylsilanyloxy-pyrimidine 
• 3188-13-4 ethyl chloromethyl ether 
• 609-12-1 ethyl 2-bromoisovalerate 
• 140-29-4 phenylacetonitrile 
• 718-08-1 ethyl 3-oxo-4-phenylbutyrate 
• 103-80-0 phenylacetyl chloride 
• 199851-91-7 6-benzyl-5-isopropyl-2-thiouracil 
• 1026065-34-8 1-Ethoxymethyl-6-(hydroxy-phenyl-methyl)-5-isopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 144410-21-9 1-(ethoxymethyl)-5-isopropyl-2-thiouracil 
• 100-52-7 benzaldehyde 
• 176519-53-2 ethyl 2-isopropyl-3-oxo-4-phenylbutanoate 
• 6921-34-2 benzylmagnesium chloride 
• 225232-14-4 6-benzyl-2,4-dichloro-5-isopropylpyrimidine 
• 1780-42-3 2,4,6-trichloro-5-isopropylpyrimidine 

Downstream Products

• 1237521-96-8 3-(3-(4-acetylphenyl)propyl)-6-benzyl-1-(ethoxymethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-92-4 6-benzyl-1-(4-(4-fluorophenyl)butyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-91-3 6-benzyl-1-(3-(4-fluorophenyl)propyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-90-2 6-benzyl-1-((4-fluorophenyl)ethyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-89-9 6-benzyl-1-(4-(4-fluorophenyl)butyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-88-8 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-87-7 6-benzyl-1-(2-(4-fluorophenyl)ethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-86-6 6-benzyl-1-(4-(4-fluorophenyl)butyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1281859-85-5 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1281859-84-4 6-benzyl-1-(2-(4-fluorophenyl)ethyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1026720-95-5 6-Benzyl-5-isopropyl-1-(2-methoxy-ethyl)-3-(2-oxo-2-phenyl-ethyl)-1H-pyrimidine-2,4-dione 
• 1027144-85-9 6-Benzyl-1-butyl-5-isopropyl-3-(2-oxo-2-phenyl-ethyl)-1H-pyrimidine-2,4-dione 
• 165960-84-9 6-benzyl-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 847995-32-8 6-benzyl-3-[4-(benzyloxy)benzoyl]-1-(ethoxymethyl)-5-isopropyl-1,2,3,4-tetrahydropyrimidine-2,4-dione 

Relevant articles and documents

New efficient and flexible synthetic route to Emivirine and its analogs

A revised synthetic route to Emivirine (MKC-442) via properly substituted β-keto ester converted from Meldrum's Acid was developed. This method could be applied to the synthesis of a variety of MKC-442 analogues and open the way for their systematic biological evaluation.

N-3 hydroxylation of pyrimidine-2,4-diones yields dual inhibitors of HIV reverse transcriptase and integrase

A new molecular scaffold featuring an N-hydroxyimide functionality and capable of inhibiting both reverse transcriptase (RT) and integrase (IN) of human immunodeficiency virus (HIV) was rationally designed based on 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) non-nucleoside RT inhibitors (NNRTIs). The design involves a minimal 3-N hydroxylation of the pyrimidine ring of HEPT compound to yield a chelating triad which, along with the existing benzyl group, appeared to satisfy major structural requirements for IN binding. In the mean time, this chemical modification did not severely compromise the compound's ability to inhibit RT. A preliminary structure-activity relationship (SAR) study reveals that this N-3 OH is essential for IN inhibition and that the benzyl group on N-1 side chain is more important for IN binding than the one on C-6.

3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

Pharmacophore and structure-activity relationships of integrase inhibition within a dual inhibitor scaffold of HIV reverse transcriptase and integrase

Rational design of dually active inhibitors against human immunodeficiency virus (HIV) reverse transcriptase (RT) and integrase (IN) has proved viable with 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) type of non-nucleoside RT inhibitors (NNRTIs). To establish the pharmacophore and study the structure-activity relationships (SAR) of integrase inhibition within a previously disclosed RT/IN dual inhibitor scaffold, new analogues featuring substitution at different sites of the HEPT ring were designed and synthesized. These studies have revealed an IN inhibition pharmacophore that is merged with the known RT pharmacophore through a shared C-6 benzyl group. Further SAR also demonstrated that optimal IN inhibition within our dual inhibitor scaffold requires a regiospecific (N-1) diketoacid (DKA)-carrying pendant with a certain length.

Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine

A novel route for the synthesis of 4,5-difunctionalized uracils using a chemo- and regioselective bromine/magnesium exchange reaction on 5-bromo-4-halogeno-2,6-dimethoxypyrimidines has been developed. Applications to the synthesis of pharmaceuticals such as oxypurinol and emivirine are reported.

Method for preparing 5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1h,3h)-dione

The invention relates to a process for the preparation of 5-(1-methylethyl)-6 -(phenylmethyl)pyrimidine-2,4(1H,3H)-dione.

ANTIVIRAL AGENTS

An antiviral agent against retroviruses exhibiting synergistic antiviral effect which comprises as active ingredients a 6-benzyl-1-ethoxy-methyl-5-substituted uracil derivative such as 6-benzyl-1-ethoxymethyl-5-isopropyluraci together with two or more sub

Regioselective alkylation and arylation at the 6-position of pyrimidine: Synthesis of 5-alkyl-6-arylmethyl-2,4-pyrimidinediones

5-Alkyl-2,4,6-trichloropyrimidines reacted with various nucleophiles to afford the regioselectivity 6-substituted pyrimidines as the major products in good yields, which were transformed to 5-alkyl-6-arylmethyl-2,4- pyrimidinediones of a key intermediate

Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine

Ethyl 2-alkyl-4-aryl-3-oxobutyrates were synthesized from the corresponding arylacetonitriles and 2-brome esters. Condensation of the butyrates with thiourea followed by treatment with chloroacetic acid afforded the 5-alkyl-6-(arylmethyl)uracils. Condensa

HEPT derivatives: 6-Benzyl-1-ethoxymethyl-5-isopropyluracil (MKC-442)

The 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) derivatives have been found to be potent and specific inhibitors of human immunodeficiency virus type 1 (HIV-1) replication in vitro. Among the compounds, MKC 442 (6-benzyl-1-ethoxymethyl-5-isopropyluracil) has recently been chosen as a candidate for clinical efficacy and safety studies in patients with the acquired immune deficiency syndrome (AIDS).