180181-02-6

Basic information

• Product Name: Boc-3-amino-2,2-dimethyl-propionic acid
• Synonyms: Boc-3-amino-2,2-dimethyl-propionic acid;3-BOCAMINO-2,2-DIMETHYL-PROPIONIC ACID;3-((tert-Butoxycarbonyl)aMino)-2,2-diMethylpropanoic acid;3-(tert-butoxycarbonyl)-2,2-dimethylpropanoic acid;Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-;2,2-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-Boc-3-amino-2,2-dimethylpropionic acid
• CAS NO: 180181-02-6
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.263
• Mol File: 180181-02-6.mol

Chemical Properties

• Boiling Point: 346.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.082±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.61±0.10(Predicted)
• CAS DataBase Reference: Boc-3-amino-2,2-dimethyl-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3-amino-2,2-dimethyl-propionic acid(180181-02-6)
• EPA Substance Registry System: Boc-3-amino-2,2-dimethyl-propionic acid(180181-02-6)

Safety Data

• Hazardous Substances Data: 180181-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-3-amino-2,2-dimethyl-propionic acid is used as a key reactant in the synthesis of cryptophycin anticancer agents. These agents are a class of natural products with potent anti-cancer properties, targeting various types of cancer cells. The compound plays a crucial role in the development of these therapeutic agents due to its unique structural features and reactivity.
In the synthesis of cryptophycin, Boc-3-amino-2,2-dimethyl-propionic acid serves as a starting material or intermediate, contributing to the formation of the final product's complex structure. The Boc protecting group ensures the selective protection of the amino group during the synthesis process, allowing for the controlled formation of the desired product. Once the cryptophycin molecule is formed, the Boc group can be removed under mild conditions, yielding the active anticancer agent.
The use of Boc-3-amino-2,2-dimethyl-propionic acid in the pharmaceutical industry highlights its importance in the development of novel and effective cancer treatments. Its unique structural features and reactivity make it a valuable building block in the synthesis of complex organic molecules, particularly in the field of anticancer drug discovery and development.

Upstream product

• 195387-08-7 methyl 3-<<(tert-butoxy)carbonyl>amino>-2,2-dimethylpropanoate 
• 204514-14-7 ethyl 2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 
• 19036-43-2 aminopivalic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1572-98-1 2-cyano-2-methyl-propionic acid ethyl ester 
• 59193-77-0 3-amino-2,2-dimethylpropionic acid ethyl ester 
• 184357-44-6 tert-butyl (3-hydroxy-2,2-dimethylpropyl)carbamate 
• 2843-19-8 3-amino-2,2-dimethylpropanoic acid, hydrochloride salt 
• 1209778-22-2 3-azido-2,2-dimethylpropionic acid 
• 13511-38-1 3-chloropivalic acid 

Downstream Products

• 204397-95-5 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-[4-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxopropoxy]phenyl]-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204397-80-8 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-[4-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxopropoxy]methyl]phenyl]-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 1333123-46-8 S-(R)-2-acetamidoethyl 3-(2-(tert-butoxycarbonylamino)-3-(3-chloro-4-methoxyphenyl)propanamido)-2,2-dimethylpropanethioate 
• 1333123-38-8 S-2-acetamidoethyl 3-((R)-3-(3-chloro-4-methoxyphenyl)-2-((2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenylocta-2,7-dienamido)propanamido)-2,2-dimethylpropanethioate 
• 666844-50-4 benzyl 3-(tert-butoxycarbonylamino)-2,2-di(methyl)propionate 

Relevant articles and documents

Isotopically labelled and unlabelled β-peptides with geminal dimethyl substitution in 2-position of each residue: Synthesis and NMR investigation in solution and in the solid state

The preparation of (S)-β2.2.3-amino acids with two Me groups in the α-position and the side chains of Ala, Val, and Leu in the β-position (double methylation of Boc-β-HAla-OMe, Boc-β-Val-OMe, and Boc-β-Leu-OMe, Scheme 2) is described. These β-amino acids and unlabelled as well as specifically 13C- and 15N-labelled 2,2-dimethyl-3-amino acid (β2.2-HAib) derivatives have been coupled in solution (Schemes 1, 3 and 4) to give protected (N-Boc, C-OMe), partially protected (N-Boc/C-OH, N-H/C-OMe), and unprotected β2.2- and β2.2.3.-hexapeptides, and β2.2- and β2.2.3-heptapeptides 1-7. NMR Analyses in solution (Tables 1 and 2, and Figs. 2-4) and in the solid state (2D-MAS NMR measurements of the fully labelled Boc-(β2.2-HAib)6-OMe ([13 C30, 15N6]-1e; Fig. 5), and TEDOR/REDOR NMR investigations of mixtures (Fig. 6) of the unlabelled Ac-(β2.2-HAib)7-OMe (4) and of a labelled derivative ([13C4,15N2]-5; Figs. 7-11, and 19), a molecular-modeling study (Figs. 13-15), and a search in the Cambridge Crystallographic Data Base (Fig. 16) allow the following conclusions: i) there is no evidence for folding (helix or turn) or for aggregation to sheets of the geminally dimethyl substituted peptide chains in solution; ii) there are distinct conformational preferences of the individual β2.2- and β2.2.3-amino acid residues: close to eclipsing around the C(O)-C(Me2(CHR)) bond (τ1.2), almost perfect staggering around the C(2)-C(3) ethane bond (τ2.3), and antiperiplanar arrangement of H(C3) and H(N) (τ3,N; Fig. 12) in the solid state; iii) the β2.2-peptides may be part of a turn structure with a ten-membered H-bonded ring; iv) the main structure present in the solid state of F3CCO(β2.2-HAib)7-OMe is a nonfolded chain (> 30 A between the termini and > 20 A between the N-terminus and the CH2 group of residue 5) with all C=O bonds in a parallel alignment (± 10°). With these structural parameters, a simple modelling was performed producing three (maybe four) possible chain geometries: one fully extended, two with parallel peptide planes (with zick-zack and crankshaft-type arrangement of the peptide bonds), and (possibly) a fourth with meander-like winding (D - G in Figs. 17 and 18).

NOVEL FERROPORTIN INHIBITORS

The invention relates to novel ferroportin inhibitors of the general formula (I) pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for the prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, such as particularly iron overload states such as in particular thalassemia and hemochromatosis.

NOVEL COMPOUND HAVING ABILITY TO INHIBIT 11B-HSD1 ENZYME OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, METHOD FOR PRODUCING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel compound or a pharmaceutically acceptable salt thereof inhibiting 11β-HSD1 enzyme activity, a preparation method of the same, and a pharmaceutical composition comprising the same as an active ingredient. Since the compound of the present invention selectively inhibits the activity of 11β-HSD1 (11β-Hydroxysteroid dehydrogenase type 1), the compound of the invention can be effectively used as a therapeutic agent for the treatment of diseases caused by the over-activation of 11β-HSD1 such as non-insulin dependent type II diabetes, insulin resistance, obesity, lipid disorder, metabolic syndrome, and other diseases or condition mediated by the excessive activity of glucocorticoid.

NOVEL COMPOUND HAVING ABILITY TO INHIBIT 11B-HSD1 ENZYME OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, METHOD FOR PRODUCING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel compound or a pharmaceutically acceptable salt thereof inhibiting 11β-HSD1 enzyme activity, a preparation method of the same, and a pharmaceutical composition comprising the same as an active ingredient. Since the compound of the present invention selectively inhibits the activity of 11β-HSD1 (11β-Hydroxysteroid dehydrogenase type 1), the compound of the invention can be effectively used as a therapeutic agent for the treatment of diseases caused by the over-activation of 11β-HSD1 such as non-insulin dependent type II diabetes, insulin resistance, obesity, lipid disorder, metabolic syndrome, and other diseases or condition mediated by the excessive activity of glucocorticoid.

SELECTIVE CALCIUM CHANNEL MODULATORS

Methods and compounds effective in ameliorating conditions characterized by unwanted calcium channel activity, particularly unwanted T- type calcium channel activity are disclosed using a series of compounds containing N-acylated cyclic amines linked to an aπl ring as shown in formula (I).

Approaches for the synthesis of functionalized cryptophycins

The first syntheses of bioactive cryptophycins functionalized at unit D were accomplished in a one-pot Staudinger reduction/cyclization step. An azido precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D cryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations. Both new cryptophycin derivatives show high biological activity in cytotoxicity assays.

One-pot synthesis of β-amino acid derivatives via addition of bis(O-silyl) ketene acetals on iminium salts

We report here our findings on a new and highly efficient strategy for the synthesis of β-amino acids involving the addition of bis(O-silyl) ketene acetals on Mannich type iminium electrophiles.

Total synthesis of cryptophycin analogues via a scaffold approach

Allylation of in situ generated β,γ-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.

PYRAZOLE DERIVATIVES, MEDICINAL COMPOSITION CONTAINING THE SAME, MEDICINAL USE THEREOF, AND INTERMEDIATE FOR PRODUCTION THEREOF

The present invention provides pyrazole derivatives represented by the general formula: wherein R1 represents H, an optionally substituted C1-6 alkyl group etc.; one of Q and T represents a group represented by the general formula: or a group represented by the general formula: while the other represents an optionally substituted C1-6 alkyl group etc.; R2 represents H, a halogen atom, OH, an optionally substituted C1-6 alkyl group etc.; X represents a single bond, O or S; Y represents an optionally substituted C1-6 alkylene group etc.; Z represents -RB, -CORC etc. in which RB represents an optionally substituted C1-6 alkyl group etc.; and RC represents an optionally substituted C1-6 alkyl group etc.,; R4 represents H, an optionally substituted C1-6 alkyl group etc.; and R3, R5 and R6 represent H, a halogen atom etc., pharmaceutically acceptable salts thereof or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT1 and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, impaired glucose tolerance, impaired fasting glycemia, diabetic complications or obesity, and a disease associated with the increase of blood galactose level such as galactosemia, and pharmaceutical compositions comprising the same, pharmaceutical uses thereof, and intermediates for production thereof.

Cryptophycins from synthesis

A cryptophycin compound is provided having the structure: Further provided are methods of producing cryptophycins by total synthesis and methods of using cryptophycins in pharmaceuticals. It is a further object of this invention to use cryptophycins to inhibit the proliferation of mammalian cells. Moreover, methods of using cryptophycins to treat neoplasia is also provided.