1202571-69-4

Basic information

• Product Name: N-benzyl-6-(3,4-dioxo-2-(pyridin-4-ylamino)cyclobut-1-enylamino)-N-(2-morpholinoethoxy)hexanamide
• CAS NO: 1202571-69-4
• Molecular Weight: 521.616
• Mol File: 1202571-69-4.mol

Chemical Properties

• CAS DataBase Reference: N-benzyl-6-(3,4-dioxo-2-(pyridin-4-ylamino)cyclobut-1-enylamino)-N-(2-morpholinoethoxy)hexanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-6-(3,4-dioxo-2-(pyridin-4-ylamino)cyclobut-1-enylamino)-N-(2-morpholinoethoxy)hexanamide(1202571-69-4)
• EPA Substance Registry System: N-benzyl-6-(3,4-dioxo-2-(pyridin-4-ylamino)cyclobut-1-enylamino)-N-(2-morpholinoethoxy)hexanamide(1202571-69-4)

Safety Data

• Hazardous Substances Data: 1202571-69-4(Hazardous Substances Data)

Upstream product

• 504-24-5 4-aminopyridine 
• 1202571-70-7 6-amino-N-benzyl-N-(2-morpholinoethoxy)hexanamide 
• 159596-50-6 3-ethoxy-4-(pyridin-4-ylamino)-cyclobut-3-ene-1,2-dione 

Relevant articles and documents

Nicotinamide phosphoribosyltransferase inhibitors, design, preparation, and structure-activity relationship

Existing pharmacological inhibitors for nicotinamide phosphoribosyltransferase (NAMPT) are promising therapeutics for treating cancer. By using medicinal and computational chemistry methods, the structure-activity relationship for novel classes of NAMPT inhibitors is described, and the compounds are optimized. Compounds are designed inspired by the NAMPT inhibitor APO866 and cyanoguanidine inhibitor scaffolds. In comparison with recently published derivatives, the new analogues exhibit an equally potent antiproliferative activity in vitro and comparable activity in vivo. The best performing compounds from these series showed subnanomolar antiproliferative activity toward a series of cancer cell lines (compound 15: IC50 0.025 and 0.33 nM, in A2780 (ovarian carcinoma) and MCF-7 (breast), respectively) and potent antitumor in vivo activity in well-tolerated doses in a xenograft model. In an A2780 xenograft mouse model with large tumors (500 mm3), compound 15 reduced the tumor volume to one-fifth of the starting volume at a dose of 3 mg/kg administered ip, bid, days 1-9. Thus, compounds found in this study compared favorably with compounds already in the clinic and warrant further investigation as promising lead molecules for the inhibition of NAMPT.

SQUARIC ACID DERIVATIVES AS INHIBITORS OF THE NICOTINAMIDE

The present application discloses novel squaric acid derivatives of the formula A: from -C(=O)-, -S(=O)2-, -C(=S)- and -P(=O)(R5)-; B: -, -O-, -NR6- and -C(=O)-NR6-; D : -, -O-, -CR7R8- and -NR9; m=0-12; n = 0-12; m+n = 1-20; p=0-2; R1 : heteroaryl, aryl; R2 : H, C1-12-alkyl, C3-12-cycloalkyl, -[CH2CH2O]1-10-(C1-6-alkyl),C1-12-alkenyl, aryl, heterocyclyl, heteroaryl; R3 : C1-12-alkyl, C3-12-cycloalkyl, -[CH2CH2O]1-10-(C1-6-alkyl), C1-12-alkenyl, aryl, heterocyclyl, heteroaryl; or R2 and R3 : N-containing heterocyclic/heteroaromatic ring; R4 and R4* : H, C1-12-alkyl, C1-12-alkenyl; and pharmaceutically acceptable salts and prodrugs thereof, and their use in the treatment of diseases/conditions caused by an elevated level of NAMPRT (inflammatory and tissue repair disorders, particularly rheumatoid arthritis, inflammatory bowel disease, asthma and CPOD, osteoarthritis, osteoporosis and fibrotic diseases; dermatosis; autoimmune diseases including systemic lupus erythematosis, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, cancer, cachexia, inflammation associated with infection and viral infections, adult respiratory distress syndrome, ataxia telengiectasia).