4026-48-6

Upstream product

• 7664-41-7 ammonia 
• 34592-47-7 L-thioproline 

Downstream Products

• 69772-54-9 (4'S,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid 
• 69772-54-9 (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid 

Relevant academic research and scientific papers

Total Synthesis of Echinomycin and Its Analogues

The first total synthesis of echinomycin (1) was accomplished by featuring the late-stage construction of the thioacetal moiety via Pummerer rearrangement and simultaneous cyclization, as well as two-directional elongation of the peptide chains to construct a C2-symmetrical bicyclic octadecadepsipeptide bridged with a sulfide linkage. This strategy can be applicable to a variety of echinomycin analogues.

Synthesis and Antiproliferative Activity Evaluation of the Disulfide-Containing Cyclic Peptide Thiochondrilline C and Derivatives

Thiochondrilline C (4) was previously isolated from Verrucisispora sp. and reported to have moderate cytotoxicity against human lung adenocarcinoma cells. Herein, we report the synthesis of thiochondrilline C by N-terminal peptide extension, oxidative disulfide bond formation, and heterocycle installation as key steps. Antiproliferative activities for the prepared natural product and several derivatives against the NCI 60 cancer cell line panel are also described. Derivative 22 was identified as a moderately potent antiproliferative agent (50% growth inhibition (GI50) = 0.2-12.2 μM) with leukemia (average GI50 = 1.8 ± 0.1 μM) and colon (average GI50 = 2.4 ± 0.3 μM) cells being most sensitive.

A convenient synthesis of N-fluorenylmethoxycarbonyl-N-methyl-L-Cysteine derivatives [Fmoc,Me-Cys(R)-OH]

The synthesis of N-fluorenylmethoxycarbonyl-N,S-dimethyl-L-Cysteine (1) [Fmoc,Me-Cys(Me)-OH] and N-fluorenylmethoxycarbonyl-N-methyl-S-acetamidomethyl-L-Cysteine (2) [Fmoc,Me-Cys(Acm)-OH] is reported. The synthesis is characterized by a convenient two-step procedure from (R)-thiazolidine-4-carboxylic acid (3) via reduction and subsequent protection. Crystals of 1, which have been analyzed by single-crystal X-ray crystallography, are obtained after a simple crystallization at the end of the process, without purification of intermediates.

Production of Stealthin C Involves an S-N-Type Smiles Rearrangement

The kinamycin family of aromatic polyketide natural products contains an atypical angucycline ring system substituted with a diazo group. The enzymatic chemistry involved in constructing both of these structural features has been largely unexplored. Here

Solution-phase synthesis and biological evaluation of triostin A and its analogues

Triostin A is a biosynthetic precursor of echinomycin which is one of the most potent hypoxia inducible factor 1 (HIF-1) inhibitors. An improved solution-phase synthesis of triostin A on a preparative scale has been achieved in 17.5% total yield in 13 ste

Cystine Diamide Analogs for the Prevention of Cystine Stone Formation in Cystinuria

Cystine analogs that improve the solubility of L-cystine in urine for treatment of cystinuria and which have the structure: and pharmaceutically acceptable salts, solvates and prodrugs thereof, wherein each R and R′ pair are independently selected from (i) or (ii);(i) R and R′ are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alcohol, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, and substituted or unsubstituted heteroaryl, or(ii) R and R′ together form a substituted or unsubstituted heterocyclic ring structure, or a substituted or unsubstituted heteroaryl ring structure;X is hydrogen, or an alkyl; and Y is O or S.

An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia

A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyphenylthiazolinylthiazolidine type of siderophore common to most strains of Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'- (2-Hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde, a key molecule involved in this synthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'- thiazoline-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin. Under the conditions reported, epimerization at the C-4' center was considerably diminished.

Anatomy of a gel. Amino acid derivatives that rigidify water at submillimolar concentrations

On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that π/π stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 °C. Other gels have a 'catastrophic' break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this 'anatomy' of a gel.

Heterocyclic inhibitors of farnesyl protein transferase

Inhibition of farnesyl protein transferase is effected by compounds of the formula its enantiomers, diastereomers, pharmaceutically acceptable salts, prodrugs or solvates thereof, wherein:, A1 and A2 are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, phenyl or substituted phenyl;, G1 is S or O;, G2 is H, -C(O)OH, -C(O)NH2, 5-tetrazolyl, -C(O)N(R7)OH or -CH2OH;, X is O or R8N;, Y and Z are each independently -CH2- or -C(O)-;, R1, R2, R3, R4, R5, R6 and R7 are each independently H or alkyl;, R1 may also be alkanoyl, R1 and A1 taken together may be -(CH2)m;, R8 is H, alkyl, phenyl, phenylalkyl, substituted phenyl, (substituted phenyl)alkyl or -C(O)R9;, R9 is H, alkyl, phenyl, phenylalkyl, substituted phenyl or (substituted phenyl)alkyl;, m is 3 or 4;, n is 0, 1 or 2;, p is 0, 1 or 2; and, q is 0 or 1, with the proviso that when p is 0, then q is also 0.