883554-71-0

Usage

Uses

Used in Organic Synthesis:
METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE is used as a building block for the synthesis of complex organic molecules, leveraging its cubane core and Boc-protected amino group to facilitate various chemical reactions and the formation of new compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE is employed as a key intermediate in the development of pharmaceuticals. Its unique structure allows for the design of novel drug candidates with potential therapeutic properties.
Used in Material Science:
METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE also finds applications in material science, where its structural features can contribute to the creation of new materials with specific properties, such as improved stability or reactivity in certain conditions.
Safety Considerations:
When handling METHYL 4-(TERT-BUTYLCARBONYLAMINO)CUBANECARBOXYLATE, it is imperative to follow proper safety protocols to prevent any adverse effects due to its chemical nature. This includes using appropriate personal protective equipment, working in well-ventilated areas, and disposing of the compound according to chemical waste management guidelines.

InChI:InChI=1/C15H19NO4/c1-13(2,3)20-12(18)16-15-8-5-9(15)7-10(15)6(8)14(5,7)11(17)19-4/h5-10H,1-4H3,(H,16,18)

Upstream product

• 24539-28-4 4-(methoxycarbonyl)-1-cubanecarboxylic acid 
• 75-65-0 tert-butyl alcohol 

Relevant academic research and scientific papers

Cubane Electrochemistry: Direct Conversion of Cubane Carboxylic Acids to Alkoxy Cubanes Using the Hofer–Moest Reaction under Flow Conditions

The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. The first electrochemical functionalisation of cubane by oxidative decarboxylative ether formation (Hofer–Moest reaction) was demonstrated. The mild conditions are compatible with the presence of other oxidisable functional groups, and the use of flow electrochemical conditions allows straightforward upscaling.

SULFINYLAMINOBENZAMIDE AND SULFONYLAMINOBENZAMIDE DERIVATIVES

Provided is a compound of Formula (I): wherein the variable groups are defined herein.

1,3 DI-SUBSTITUTED CYCLOBUTANE OR AZETIDINE DERIVATIVES AS HEMATOPOIETIC PROSTAGLANDIN D SYNTHASE INHIBITORS

A compound of formula (I), wherein R, R1, R2, R3, Y, Y1, a, X, and Z are as defined herein. The compounds of the present invention are inhibitors of hematopoietic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne Muscular Dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

SUBSTITUTED N-BICYCLO-2-ARYL-QUINOLIN-4-CARBOXAMIDES AND USE THEREOF

The present application relates to novel substituted N-bicyclo-2-arylquinoline-4-carboxamide derivatives, to processes for preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases, and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of fibrotic and inflammatory disorders.

Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins

A streamlined total synthesis of N14-desacetoxytubulysin H (Tb1) based on a C-H activation strategy and a short total synthesis of pretubulysin D (PTb-D43) are described. Applications of the developed synthetic strategies and technologies to the synthesis of a series of tubulysin analogues (Tb2-Tb41 and PTb-D42) are also reported. Biological evaluation of the synthesized compounds against an array of cancer cells revealed a number of novel analogues (e.g., Tb14), some with exceptional potencies against certain cell lines [e.g., Tb32 with IC50 = 12 pM against MES SA (uterine sarcoma) cell line and 2 pM against HEK 293T (human embryonic kidney) cell line], and a set of valuable structure-activity relationships. The highly potent cytotoxic compounds discovered in this study are highly desirable as payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies.

DESACETOXYTUBULYSIN H AND ANALOGS THEREOF

In one aspect, the present disclosure provides tubulysin analogs of the formula (I) wherein R1, R2, R3, R4, X1, X2, X3, and A1 are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein.

Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere

Pharmaceutical and agrochemical discovery programs are under considerable pressure to meet increasing global demand and thus require constant innovation. Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market place, but an obvious omission is that of the Platonic solid cubane. Eaton, however, suggested that this molecule has the potential to act as a benzene bioisostere. Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues displayed equal bioactivity, and the fifth one demonstrated only partial efficacy. Ramifications from this study are best realized by reflecting on the number of bioactive molecules that contain a benzene ring. Substitution with the cubane scaffold where possible could revitalize these systems, and thus expedite much needed lead candidate identification.