Synthesis of Heterocyclic Thiourea Compounds with Amino Acid Side Chain as Nonnucleoside Inhibitors of HIV‐1 Reverse Transcriptase

Heterocyclic thioureas having an amino acid ester side chain were prepared in two steps with overall yields of 65–85%. Condensation of a substituted heterocyclic amine with thiocarbonyldiimidazole, followed by treatment with an amino acid methyl ester hydrochloride in DMF, yielded the desired heterocyclic thioureas as crystalline solids. Amino acid esters such as glycine, leucine, valine, phenyl alanine, and tryptophan were used to prepare these thioureas.     

Synthesis and Anti-HIV-1 Reverse Transcriptase Activity of Triphosphates of Penciclovir and β-D-Dioxolane-Guanine

Abstract

The synthesis of R- and S-9-(4-Hydroxy-3-hydroxymethyl-but-l-yl)guanine (PCV) and (?)-β-D-dioxolane-guanine (DXG) triphosphate and their enzyme inhibitory activity is descibed.     

The QSAR Research of Pyrrolobenzothiazepinones and Pyrrolobenzo-xazepinones-Novel and Specific Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

IntroductionQSARisoneofthevaluablemeansindIugdedgne~allyfOrthoSesubStrateSwhicharenoknonclearly'ThetIadihonalQSARwasprDPagaIedbyHanschandFuitawhicheInPloyedmultiPlelinearregressiontechitiquestoobtalnqndtativerelationshiPs,ReCentiysome3DDSANmethodsareproposedwhichcantreastericandeleCtrnicproPertiessimultaneouslyinamorepraedcalmannr.TwoofthemoStsuccesthe3DQSARmdsodsareCoMFA[l],un-3D[2].AJthoughgreatPrOgresshasbenaCqulwttheSemethodshavehencrihdzedandshouldnillbeconsideredinthot…     

Synthesis of a Novel Series of S-Alkyl Thiobenzoate Compounds as Farnesyltransferase Inhibitors

S-akyl thiobenzoate compounds were designed as farnesyltransferase (FTase) inhibitors. An effective synthetic method was explored. The structures of the target compounds were elucidated by NMR spectral and elemental analysis.     

Synthesis and Biological Evaluation of Novel 1, 5-Diarylpyrazole-3-carboxamide Compounds as Inhibitors of ALK5

Many diaryl or triaryl substituted imidazoles and triazoles are known to be selective inhibitors of transforming growth factor β1(TGF-β1) type 1 receptor (ALK5)1-3. SB-431542, one of the leading compound of 2-pyridyl substituted triarylimidazole, is an …     

One‐Pot Synthesis and Hydroxylaminolysis of Asymmetrical Acyclic Nitrones

Abstract

Aromatic aldehydes 1 were reductively aminated to the corresponding secondary amines 2 using NaBH₄ in methanol in good yields. Amines 2 were oxidized with H₂O₂‐WO₄ ^2? regioselectively to nitrones 3, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes 4 and benzyl or methyl hydroxylamine hydrochlorides 5.     

Synthesis of Thiourea‐Bridged Cluster Glycoside Calixarenes

Thiourea‐bridged peracetylated glycoside calixarenes have been smoothly synthesized by the addition reactions of tetraacetylglycosyl isothiocyanates with amidoamine derivatives of calix[4]resorcinarene and p‐tert‐butylcalix[n]arenas (n=6, 8) in high yields (40–75%). All the glycoside‐containing calixarenes were characterized by ¹H NMR, IR spectroscopy, and elemental analysis.     

Synthesis of Novel Asymmetrical 1,4‐Dihydropyridine Derivatives

Asymmetrical 1,4‐dihydropyridine esters 3a and 3i–k were synthesized from the symmetrical precursor 1 through the intermediate 2‐bromomethyl derivative 2. Then, compound 3a was subjected to a different transformation for preparation of 1,4‐dihydropyridine derivatives 3b–h.     

Hiv-1 Specific Reverse Transcriptase Inhibitors: why are Tsao-Nucleosides so Unique?

1. INTRODUCTION

AIDS will still be one of the most important challenges for the Scientific Community in the approaching new century. Since the identification, in 1983-84,^1,2 of human immunodeficiency virus (HIV) as the etiological agent of AIDS, significant progress has been made in the treatment of HIV-infected patients. This has been in part due to the discovery and clinical use of an increasing number of anti-HIV drugs. However, while highly active antiretroviral therapy (HAART)³ approaches have reduced the morbidity and mortality, the intertwined problems of drug induced viral resistance, poor compliance with complex regimens and therapy failure continue. Therefore, there remains a pressing need for the development of new antiviral agents that can be used not only as first line therapeutic candidates, but also in the antiretroviral-experienced patient population.     

Synthesis of Novel Photochromic 6‐Benzyloxo‐spirobenzopyran Compounds

The synthesis of four novel derivatives of 1′,3′,3′‐trimethylspiro‐[2H‐1]‐benzopyran‐6‐benzyloxo‐2,2′‐indoline is reported. The synthetic approach to these compounds involves the preparation of the key compound, 3‐formyl‐4‐hydroxybenzophenone, by means of the Reimer–Tiemann reaction. The photochromic compounds were isolated and characterized by ¹H and ¹³C NMR as well as FT‐IR and UV‐VIS spectrometry. Comparative studies performed in these compounds showed a higher molar extinction coefficient and red shift of maximum absorption wavelength when the benzyloxo group is introduced in the spirobenzopyran molecule.     

Synthesis of 3‐Aryl‐5‐t‐butylsalicylaldehydes and their Chiral Schiff Base Compounds

Six meta‐substituted salicylaldehyde compounds have been prepared in 68–90% yields by the Suzuki–Miyaura coupling reaction using 3‐bromo‐5‐t‐butylsalicylaldehyde (1a) and arylboronic acids (2a–f) as reactants. Among the obtained products, 3‐(4‐fluorophenyl)‐5‐t‐butylsalicylaldehyde (3b), 3‐(4‐methylphenyl)‐5‐t‐butylsalicylaldehyde (3d), 3‐(1‐naphthyl)‐5‐t‐butylsalicylaldehyde (3e), and 3‐(2‐naphthyl)‐5‐t‐butylsalicylaldehyde (3f) have not been reported so far. A series of new Schiff base ligands (L1–L10) were obtained in 51–89% yields from these salicylaldehyde derivatives.     

Synthesis and Evaluation of Coumarin–Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors

A series of coumarin–resveratrol hybrids, 3-arylcoumarin derivatives 3a–u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities.     

α-Haloalkyl Haloformates and Related Compounds 3.1 A Facile Synthesis of Symmetrical and Unsymmetrical Ureas via Chloromethyl Carbamates

Chloromethyl carbamates were prepared by the reaction of chloromethyl chloroformates with amines and found to produce mono-, symmetrically or unsymmetrically di-and trisubstituted ureas including their N-hydroxy and N-alkoxy derivatives in moderate to good yield.     

Cupric Chloride–Catalyzed Synthesis of Symmetrical Azo Compounds from Primary Aromatic Amines

Symmetrical azo compounds were synthesized from primary aromatic amines using n-BuMgBr as a base, oxygen as an oxidant, and CuCl₂ as a catalyst.