16689-34-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Isopropylidenecarbazic acid tert-butyl ester is used as a key intermediate in the synthesis of various therapeutic compounds. Its unique structure allows for the development of new drugs with potential applications in treating different medical conditions.
Used in the Synthesis of Pyrazole Derivatives:
3-Isopropylidenecarbazic acid tert-butyl ester is used as a starting material for the preparation of pyrazole derivatives. These derivatives have shown potential as therapeutics for immune thrombocytopenias, a condition characterized by a low platelet count in the blood, leading to an increased risk of bleeding.
Used in the Synthesis of HIV-1 Protease Inhibitors:
3-Isopropylidenecarbazic acid tert-butyl ester is also utilized in the synthesis of stereopure hydroxylactam-based HIV-1 protease inhibitors. These inhibitors play a crucial role in the treatment of HIV/AIDS by blocking the activity of the HIV-1 protease enzyme, which is essential for the replication of the virus.

Upstream product

• 870-46-2 t-butoxycarbonylhydrazine 
• 77-76-9 2,2-dimethoxy-propane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 67-64-1 acetone 

Downstream Products

• 561067-07-0 N-ethyl-N'-isopropylidene-hydrazinecarboxylic acid tert-butyl ester 
• 561067-10-5 N-benzyl-N'-isopropylidene-hydrazinecarboxylic acid tert-butyl ester 
• 561067-08-1 tert-butyl 2-(propan-2-ylidene)-1-propylhydrazine-1-carboxylate 
• 26177-51-5 (4-methylbenzyl)hydrazine hydrochloride 
• 286373-56-6 1-Benzyloxycarbonyl-2-(tert-butoxycarbonyl)-1-isopropylhydrazine 
• 162739-75-5 2-(tert-butyl) 1-(4-nitrophenyl) 1-isopropylhydrazine-1,2-dicarboxylate 
• 1608125-58-1 tert-butyl-1-(cyclohexylmethyl)-2-(propan-2-ylidene)hydrazine carboxylate 
• 70629-60-6 isopropylhydrazine hydrochloride 
• 1429433-52-2 Boc-AzaVal-Met-Gly-OPhe-OH 

Relevant academic research and scientific papers

Synthesis of Macrocycles Derived from Substituted Triazines

A triazine ring derivatized with morpholine, an N-alkyl-N′-BOC-hydrazine (alkyl=isopropyl or benzyl) and the diethylacetal of glycinylpropionaldehyde undergoes spontaneous dimerization in good yields upon acid-catalyzed deprotection. The resulting 24-member macrocycles can be characterized by NMR spectroscopy, mass spectrometry, and single crystal X-ray diffraction. In the solid state, both homodimers adopt a taco-like conformation. Although each shows π–π stacking between the triazine rings, different patterns of hydrogen bonds emerge. The crystal structure of the isopropyl dimer shows that it includes two molecules of trifluoracetic acid per macrocycle. The trifluoroacetate anion charge balances the protonated triazines, which engage in bifurcated hydrogen bonds with the carbonyl acceptor of the distant glycine. This carbonyl also forms a hydrogen bond with the NH of the proximate glycine. The crystal structure of the benzyl derivative does not include trifluoracetic acid. Instead, two hydrogen bonds form, each between a glycine NH and the lone pair of the C=N nitrogen of the hydrazine group. In the solid state, both molecules present the alkyl side chains and morpholine groups in close proximity. A heterodimer is accessible in approximately statistical yields—along with both homodimers—by mixing the two protected monomers prior to subjecting them to deprotection.

Crystallographic Insights into the Synthesis and Magnetic Properties of Oxoverdazyl Radicals Functionalized by Benzoic Acid

The synthesis and crystallization of two verdazyl radicals, 1,5-dimethyl-3-(4′-carboxyphenyl)-6-oxoverdazyl HIMe and 1,5-diisopropyl-3-(4′-carboxyphenyl)-6-oxoverdazyl HIiPr, are described. The electrochemical studies reveal that the oxidation of the two radicals is reversible, whereas their reduction is irreversible. The EPR spectrum of both radicals essentially exhibits a nine-line pattern related to the mean hyperfine interaction of the unpaired electron with the nitrogen atoms of the verdazyl cycle. The single-crystal X-ray diffraction of the intermediates towards HIiPr allows a fine description of the cyanoborane adduct, which is the key intermediate of this synthesis. The verdazyl radicals themselves are obtained as single crystals. In the case of HIiPr, depending on the solvent, two polymorphs are crystallized. The structure resolution reveals that, in the solid state, the organization of the verdazyl radicals is governed by both H-bonding and π–π interactions and is reminiscent of the H-bonded structures that can be present in solution. Within the 1D π stacks observed in the three compounds, the verdazyl–verdazyl distance varies from 4.88 ? in HIMe to 7.90 ? in HaIiPr. This modulation of the distance strongly influences the antiferromagnetic intermolecular exchange interaction between π-stacked radicals, which goes from J = –90 cm–1 (H = –JΣSiSi+1) for HIMe to –12.96(3) cm–1 for HbIiPr and –0.92 cm–1 for HaIiPr.

Design and synthesis of novel methoxypyridine-derived gamma-secretase modulators

The evolution of gamma-secretase modulators (GSMs) through the introduction of novel heterocycles with the goal of aligning activity for reducing the levels of Aβ42 and properties consistent with a drug-like molecule are described. The insertion of a methoxypyridine motif within the tetracyclic scaffold provided compounds with improved activity for arresting Aβ42 production as well as improved properties, including solubility. In vivo pharmacokinetic analysis demonstrated that several compounds within the novel series were capable of crossing the BBB and accessing the therapeutic target. Treatment with methoxypyridine-derived compound 64 reduced Aβ42 levels in the plasma of J20 mice, in addition to reducing Aβ42 levels in the plasma and brain of Tg2576 mice.

Synthesis of Highly Substituted 1,2-Diazetidin-3-ones, Small-Ring Scaffolds for Drug Discovery

1,2-Diazetidin-3-ones are readily accessible, small ring scaffolds that upon functionalization have the potential to produce diverse 3-dimensional structures for drug discovery. Thus, treatment of diazo hydrazides, obtained from simple hydrazides and malonyl half ester derivatives, followed by diazo transfer, with catalytic amounts of rhodium(II) acetate dimer results in intramolecular carbenoid N?H insertion to give 1,2-diazetidin-3-ones. Although subsequent functionalization reactions could be hampered by the lability of the 4-membered ring, a wide range of new derivatives was available by deprotection at N-1, and subsequent amide or urea formation. The structures of four four-membered rings was confirmed by X-ray crystallography; the compounds showed modest growth inhibitory activity in mammary carcinoma cells.

Antiviral drug and drug composition thereof

The invention relates to an antiviral drug and a drug composition thereof, specially relates to a drug against human immunodeficiency virus (HIV) and a drug composition thereof, and particularly relates to a drug capable of serving as a retrovirus proteas

Towards a general synthesis of di-aza-amino acids containing peptides

While the incorporation of one aza-amino acid in peptides has been proved to be beneficial for inducing a structure constraint, increasing the resistance towards proteolysis and improving the biological activity, only very rare examples of the incorporation of two or more consecutive aza-amino acids have been reported. In this work, we demonstrate that this fact is probably due to the unsuspected difficulty in synthesizing such peptide analogues, as illustrated by the synthesis of tripeptide derivatives containing two consecutive aza-amino acids. Herein, we report some general guidelines regarding the activation and the coupling of alkyl-hydrazides either mutually or with a natural amino acid, taking into account their nucleophilicity and the nature of their side chains.

1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones and 1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-ones as PDE1 Inhibitors

The present invention provides 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones and 1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-ones of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

PYRAZOLOPYRIMIDINES AS INHIBITORS OF GLUCOCORTICOID RECEPTOR TRANSLOCATION

Provided herein are compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of Glucocorticoid Receptor (GR) translocation. Furthermore, the subject compounds and compositions are useful for the treatment of diseases involved in the hypothalamic-pituitary-adrenal (HPA) axis.

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).

Antiviral drug and its pharmaceutical composition

The invention relates to an antiviral medicine and a medicine composition thereof, in particular relates to an anti-human immunodeficiency virus (HIV) medicine and a medicine composition thereof, and especially relates to a medicine which can be taken as