77369-60-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Tert-Butyl (4-chloro-2-butyn-1-yl)carbamate is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its ability to act as a carbamate protecting group. This allows for selective deprotection under mild conditions, facilitating the synthesis of complex molecules.
Used in Organic Synthesis as a Protecting Group:
In the field of organic synthesis, tert-Butyl (4-chloro-2-butyn-1-yl)carbamate is used as a carbamate protecting group for selective deprotection. This feature is crucial for the synthesis of sensitive compounds, where the protection and subsequent deprotection of functional groups are necessary to prevent unwanted side reactions.
Used in the Development of Novel Insecticides:
Tert-Butyl (4-chloro-2-butyn-1-yl)carbamate is used as a reversible inhibitor of cholinesterases, making it a potential candidate for the development of novel insecticides. Its ability to inhibit cholinesterases can lead to the development of new classes of insecticides with unique modes of action.
Used in the Development of Neuroprotective Agents:
Due to its cholinesterase inhibitory properties, tert-Butyl (4-chloro-2-butyn-1-yl)carbamate is also considered for the development of neuroprotective agents. These agents could potentially be used in the treatment of neurodegenerative diseases where cholinergic dysfunction is implicated.
Used in Synthetic Chemistry as a Building Block:
The versatile chemical structure and reactivity of tert-Butyl (4-chloro-2-butyn-1-yl)carbamate make it a valuable building block in synthetic chemistry. It can be used to construct a wide range of complex organic molecules, contributing to the advancement of chemical research and the development of new compounds with various applications.

Upstream product

• 34619-03-9 tert-butyldicarbonate 
• 77369-59-6 1-Amino-4-chloro-2-butyne hydrochloride 
• 144-55-8 sodium hydrogencarbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 87876-05-9 4-chloro-2-butyn-1-amine 

Downstream Products

• 404859-39-8 C₂₆H₃₀N₂O₄ 
• 127953-51-9 diethyl (S)-2-<4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-butynyl>-2-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>propanedioate 

Relevant academic research and scientific papers

Introduction of Peripheral Carboxylates to Decrease the Charge on Tm3+ DOTAM-Alkyl Complexes: Implications for Detection Sensitivity and in Vivo Toxicity of PARACEST MRI Contrast Agents

A series of structurally modified Tm3+ DOTAM-alkyl complexes as potential PARACEST MRI contrast agents has been synthesized with the aim to decrease the overall positive charge associated with these molecules and increase their biocompatibility. Two types of structural modification have been performed, an introduction of terminal carboxylate arms to the alkyl side chains and a conjugation of one of the alkyl side chains with aspartic acid. Detailed evaluation of the magnetic resonance imaging chemical exchange contrast associated with the structurally modified contrast agents has been performed. In contrast to the acutely toxic Tm3+ DOTAM-alkyl complexes, the structurally modified compounds were found to be tolerated well during in vivo MRI studies in mice; however, only the aspartic acid modified chelates produced an amide proton-based PARACEST signal. (Figure Presented).

MACROCYCLES AS PIM INHIBITORS

The invention relates to compounds of formula (1), and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication

The redesign of azamacrocyclic CXCR4 chemokine receptor antagonists resulted in the discovery of novel, small molecule, orally bioavailable compounds that retained T-tropic (CXCR4 using, X4) anti-HIV-1 activity. A structure-activity relationship (SAR) was determined on the basis of the inhibition of replication of X4 HIV-1 NL4.3 in MT-4 cells. As a result of lead optimization, we identified (S)-N′-((1H-benzo[d]imidazol-2-yl)methyl)- N′-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine (AMD070) 2 as a potent and selective antagonist of CXCR4 with an IC50 value of 13 nM in a CXCR4 125I-SDF inhibition binding assay. Compound 2 inhibited the replication of T-tropic HIV-1 (NL4.3 strain) in MT-4 cells and PBMCs with an IC50 of 2 and 26 nM, respectively, while remaining noncytotoxic to cells at concentrations exceeding 23 μM. The pharmacokinetics of 2 was evaluated in rat and dog, and good oral bioavailability was observed in both species. This compound represents the first small molecule orally bioavailable CXCR4 antagonist that was developed for the treatment of HIV-1 infection.

CHEMICAL COMPOUNDS

The present invention provides novel compounds that demonstrate protective effects on target cells from HIV infection in a manner as to bind specifically to the chemokine receptor, and which affect the binding of the natural ligand or chemokine to a receptor such as CXCR4 and/or CCR5 of a target cell.

Chemokine receptor binding heterocyclic compounds with enhanced efficacy

The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

Inhibition of bovine plasma amine oxidase by 1,4-diamino-2-butenes and -2-butynes

Bovine plasma amine oxidase (BPAO) was previously shown to be irreversibly inhibited by propargylamine and 2-chloroallylamine. 1,4-Diamine versions of these two compounds are here shown to be highly potent inactivators, with IC50 values near 20 μM. Mono-N-alkylation or N,N-dialkylation greatly lowered the inactivation potency in every case, whereas the mono-N-acyl derivatives were also weaker inhibitors and enzyme activity was recoverable. The finding that the bis-primary amines 1,4-diamino-2-butyne (a known potent inhibitor of diamine oxidases) and Z-2-chloro-1,4-diamino-2-butene are potent inactivators of BPAO is suggestive of unexpected similarities between plasma amine oxidase and the diamine oxidases and implies that it may be unwise to attempt to develop selective inhibitors of diamine oxidase using a diamine construct.

Halogenated amidino amino acid deviratives useful as nitric oxide synthase inhibitors

The current invention discloses halogenated amidino amino acid derivatives useful as nitric oxide synthase inhibitors, and pharmaceutically acceptable salts thereof.

SYNTHESIS OF MONO- AND DI-ACYLATED L-2,6-DIAMINO-4-HEXYNOIC ACID POTENTIAL DERIVATIVES FOR PREPARATION OF (3)H-LABELLED LYSINE CONTAINING PEPTIDES

The selective acylation of the 6-amino group of 2,6-diamino-4-hexynoic acid was obtained in high overall yield by a simple approach instead of copper complex method.