149552-52-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-(4-BROMOPHENYL)ETHYL ISOCYANATE is utilized as a reagent in organic synthesis for the production of pharmaceuticals. Its ability to form ureas and carbamates through reactions with nucleophiles makes it a valuable component in the development of various medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-(-)-1-(4-BROMOPHENYL)ETHYL ISOCYANATE is employed as a reagent in organic synthesis for the creation of agrochemicals. Its role in forming key chemical structures is essential for the development of products used in agricultural applications.
Used as a Building Block in Organic Chemistry:
(S)-(-)-1-(4-BROMOPHENYL)ETHYL ISOCYANATE is used as a building block in organic chemistry due to its reactivity with nucleophiles. This characteristic allows it to contribute to the synthesis of a wide range of organic compounds, expanding its applications beyond the pharmaceutical and agrochemical industries.

InChI:InChI=1/C9H8BrNO/c1-7(11-6-12)8-2-4-9(10)5-3-8/h2-5,7H,1H3/t7-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 24358-62-1 (R)-1-(4-bromophenyl)ethylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 27298-97-1 (S)-1-(4-bromophenyl)ethylamine 
• 24358-62-1 1-(4-bromophenyl)ethylamine 
• 1118-02-1 trimethylsilyl isocyanate 
• 1585-07-5 1-bromo-4-ethylbenzene 

Downstream Products

• 1110641-99-0 (R)-3-((R)-1-(2',4'-difluoro-[1,1'-biphenyl]-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one 
• 1110642-51-7 (S)-3-((R)-1-(2',4'-difluoro-[1,1'-biphenyl]-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one 
• 1114086-18-8 (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-fluorophenyl)-1,3-oxazinan-2-one 
• 1321599-81-8 (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-fluorophenyl)-1,3-oxazinan-2-one 
• 1110641-76-3 (S)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one 

Relevant academic research and scientific papers

Benzylic C-H isocyanation/amine coupling sequence enabling high-throughput synthesis of pharmaceutically relevant ureas

C(sp3)-H functionalization methods provide an ideal synthetic platform for medicinal chemistry; however, such methods are often constrained by practical limitations. The present study outlines a C(sp3)-H isocyanation protocol that enables the synthesis of diverse, pharmaceutically relevant benzylic ureas in high-throughput format. The operationally simple C-H isocyanation method shows high site selectivity and good functional group tolerance, and uses commercially available catalyst components and reagents [CuOAc, 2,2′-bis(oxazoline) ligand, (trimethylsilyl)isocyanate, andN-fluorobenzenesulfonimide]. The isocyanate products may be used without isolation or purification in a subsequent coupling step with primary and secondary amines to afford hundreds of diverse ureas. These results provide a template for implementation of C-H functionalization/cross-coupling in drug discovery.

Alkyl Isocyanates via Manganese-Catalyzed C-H Activation for the Preparation of Substituted Ureas

Organic isocyanates are versatile intermediates that provide access to a wide range of functionalities. In this work, we have developed the first synthetic method for preparing aliphatic isocyanates via direct C-H activation. This method proceeds efficiently at room temperature and can be applied to functionalize secondary, tertiary, and benzylic C-H bonds with good yields and functional group compatibility. Moreover, the isocyanate products can be readily converted to substituted ureas without isolation, demonstrating the synthetic potential of the method. To study the reaction mechanism, we have synthesized and characterized a rare MnIV-NCO intermediate and demonstrated its ability to transfer the isocyanate moiety to alkyl radicals. Using EPR spectroscopy, we have directly observed a MnIV intermediate under catalytic conditions. Isocyanation of celestolide with a chiral manganese salen catalyst followed by trapping with aniline afforded the urea product in 51% enantiomeric excess. This represents the only example of an asymmetric synthesis of an organic urea via C-H activation. When combined with our DFT calculations, these results clearly demonstrate that the C-NCO bond was formed through capture of a substrate radical by a MnIV-NCO intermediate.

CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1

This invention relates to novel compounds of the Formula (I), (II), (II-A), (Il-B), (ll-C), (ll-D), (III). (III-A). (IIIl-B). (IIl-C). (IIl-D), (III-E) (IV), (IV-A), (IV-B). (IV-C), (IV-D). (V), (V-A), (V-B), (V-C), (V-D), pharmaceutically acceptable salt

CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1

This invention relates to novel compounds of the Formula Ik, Im1, Im2, Im5, In1, In2, In5, Io1, Io2, Io5, Ip1, Ip3, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11β-HSD1 in mammals. The invention further relates to pharmaceutical compositions of the novel compounds and methods for their use in the reduction or control of the production of cortisol in a cell or the inhibition of the conversion of cortisone to cortisol in a cell.

CYCLIC INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE 1

This invention relates to novel compounds of an 11 β-HSD1 inhibitor disclosed herein, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful for the therapeutic treatment of diseases associated with the modula

SYNTHESIS OF INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1

Disclosed are syntheses of 11 beta-HSD1 inhibitors and corresponding intermediates that are promising for the treatment of a variety of disease states including diabetes, metabolic syndrome, obesity, glucose intolerance, insulin resistance, hyperglycemia, hypertension, hypertension-related cardiovascular disorders, hyperlipidemia, deleterious gluco-corticold effects on neuronal function (e.g. cognitive impairment, dementia, and/or depression), elevated intra-ocular pressure, various forms of bone disease (e.g., osteoporosis), tuberculosis, leprosy (Hansen's disease), psoriasis, and impaired wound healing (e.g., in patients that exhibit impaired glucose tolerance and/or type 2 diabetes).

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity, wherein X1, X2, X3, X4, X5, R5, R6, R7, R8a, R8b, R9, Z1, Z2 and L are as defined in the description.

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

Synthesis of rigid receptors based on triphenylene ketals

The synthesis of rigid receptors based on triphenylene ketals, including some improved procedures, is described in detail. Since chemical transformations are strongly influenced by the rigid character and steric bulkiness of the receptors, the constructio

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.