98105-45-4

Usage

Uses

Used in Pharmaceutical Industry:
BOC-ACHPA is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to mimic natural amino acids and participate in peptide bond formation. Its unique cyclohexyl group provides specific steric and electronic properties that can be advantageous in the design of novel drug molecules.
Used in Research and Development:
In the field of research and development, BOC-ACHPA serves as a valuable tool for studying peptide synthesis and the development of new methodologies for peptide bond formation. Its reactivity and structural features make it an interesting subject for exploring new chemical reactions and mechanisms.
Used in Chemical Synthesis:
BOC-ACHPA is used as a building block in the synthesis of complex organic molecules and compounds. Its cyclohexyl moiety and statine core can be incorporated into various chemical structures, providing a versatile platform for the creation of new molecules with potential applications in different industries.
Used in Material Science:
In material science, BOC-ACHPA can be utilized in the development of new materials with specific properties. Its unique structure may contribute to the formation of novel polymers, coatings, or other materials with tailored characteristics for various applications, such as improved mechanical strength or specific interactions with biological systems.

InChI:InChI=1/C16H29NO5/c1-16(2,3)22-15(21)17-12(13(18)10-14(19)20)9-11-7-5-4-6-8-11/h11-13,18H,4-10H2,1-3H3,(H,17,21)(H,19,20)/t12-,13-/m0/s1

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 98105-41-0 methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate 
• 98105-42-1 (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 98105-43-2 (S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoic acid ethyl ester 
• 98105-43-2 (3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester 
• 72155-48-7 (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid 
• 112271-08-6 (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester 
• 72155-46-5 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-3-hydroxy-5-phenylpentanoic acid ethyl ester 

Downstream Products

• 118388-56-0 ((1S,2S)-3-{(S)-1-[3-(Benzyloxycarbonylamino-methyl)-benzylcarbamoyl]-3-methyl-butylcarbamoyl}-1-cyclohexylmethyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester 
• 137769-83-6 (S)-2-[(2S,3S)-2-((3S,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoylamino)-3-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester 
• 113209-06-6 Boc-ACHP-Ile-(3-pyridylmethyl)amide 
• 124278-65-5 (S,S)-γ-amino-β-hydroxy-N-<2-(4-morpholinyl)ethyl>cyclohexane pentanamide 
• 119357-93-6 (3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide 
• 119379-17-8 (3S,4S)-4-amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide 
• 116326-39-7 ES-6864 
• 128972-24-7 (S)-2-((3S,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoylamino)-4-methyl-pentanoic acid 
• 125447-50-9 (3S,4S)-4-Amino-5-cyclohexyl-3-hydroxy-pentanoic acid {(S)-3-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide 
• 128972-25-8 ((1S,2S)-1-Cyclohexylmethyl-2-hydroxy-3-{(S)-3-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 128972-39-4 (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-isobutyl-6-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-acetylamino]-pentanoic acid {(S)-3-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide 
• 128972-29-2 (S)-2-Benzyloxycarbonylamino-6-[(S)-2-((3S,4S)-4-tert-butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoylamino)-4-methyl-pentanoylamino]-hexanoic acid benzyl ester 
• 128972-43-0 4-((S)-2-{(3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-isobutyl-6-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoylamino}-4-methyl-pentanoylamino)-butyric acid 
• 128972-40-7 (3S,4S)-5-Cyclohexyl-3-hydroxy-4-[2-(8-isobutyl-6-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridin-3-yl-propionylamino]-pentanoic acid {(S)-3-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butyl}-amide 

Relevant academic research and scientific papers

New potential renin inhibitors with dipeptide replacements in the molecule

A series of eight non-peptidic potential renin inhibitors have been designed and synthesized. All of them contain dipeptide replacement: (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA) in their molecules. Four among them comprise two additional analogs of dipeptide: (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA) and (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine, Sta). All of the synthesized compounds contain also hydrophobic portions to receive a moderate lipophilicity of the molecules. Inhibitory activity of the compounds was measured in vitro by HPLC determination of Leu-Val-Tyr-Ser released from the N-acetyltetradecapeptide substrate by renin in the presence of the inhibitor. Asp-α(OEt)-(S,S)-ACHPA-εAhx-Iaa (23) shows inhibitory activity (7%) at the concentration of 1.0 × 10-2 M. The other synthesized compounds show no inhibitory activity up to this concentration.

1,2,4-Triazolopyrazine Derivatives with Human Renin Inhibitory Activity. 1. Synthesis and Biological Properties of Alkyl Alcohol and Statine Derivatives

A series of 1,2,4-triazolopyrazine derivatives with human renin inhibitory activity, which incorporate (1S,2S)-2-amino-1,3-dicyclohexyl-1-hydroxypropane, statine (Sta), and (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA) transition-state mimetics, have been prepared.Structure-activity relationships for renin inhibitory activity in the series are consistent with the 2-pyrazin-3-yl>-3-(3-pyridyl)propionic acid moiety 10b acting as a non-peptidic replacement for the P4-P2 (Pro-Phe-His) residues of the natural substrate angiotensinogen.Compounds 12m, 12o, and 12q were potent inhibitors of partially purified human renin (IC50 values 1.7, 6.8, and 3.7 nM, respectively), and also effectively lowered blood pressure in anesthetized, sodium depleted marmosets following intravenous administration.On oral administration however, no blood pressure lowering activity could be detected, and absorption studies in bile duct cannulated rats indicate that this may be due primarily to poor oral absorption, rather than rapid biliary excretion.The reason for the observed poor oral activity is not clear, but it seems unlikely that poor aqueous solubility or metabolic instability to gut enzymes are rate-determining, and other factors such as high molecular weight may also be very important.

Tripeptide renin inhibitors with N-terminal ureido or sulfamido groups

Tripeptide enzyme inhibitors of the formula:*(formula 01)* which have N-terminal ureas or sulfamides incorporating polar groups, and analogs thereof, which inhibit renin and are useful for treating various forms of renin-associated hypertension and conges

Renin inhibitors containing histidine replacments

Peptides of the formula: which comprises novel elements replacing the His(9) sequence in renin-inhibitory peptides based on substrate analogy, which have improved bioavail-ability and pharmacodynamic properties; compositions containing these renin-inhibitory peptides, optionally with other antihypertensive agents; and methods of treating hypertension or congestive heart failure or of establishing renin as a causative factor in these problems employing the novel peptides.

Renin Inhibitors. Syntheses of Subnanomolar, Competitive, Transition-State Analogue Inhibitors Containing a Novel Analogue of Statine

Analogues of the renin octapeptide substrate were synthesized in which replacement of the scissile dipeptide with (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (statine, Sta) transformed the substrate sequence into potent, transition-state analogue, competitive inhibitors of renin.Synthesis and incorporation of the cyclohexylalanyl analogue of Sta, (3s,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA), gave the most potent inhibitors of renin yet reported, including N-isovaleryl-L-histydyl-L-prolyl-L-phenylalanyl-L-histydyl-ACHPA-L-leucyl-L-phenylalanyl amide , with renin inhibitions of Ki=1.6 * 10-10 M (human kidney renin), IC50=1.7 * 10-10 M (human plasma renin), IC50=1.9 * 10-9 M (dog plasma renin), and IC50=2.1 * 10-8 M (rat plasma renin).This inhibitor 3, containing ACHPA, was 55-76 times more potent vs. human renin than the comparable Sta-containing inhibitor 1 and 17 times more potent vs. dog renin than 1.Inhibitor 3 lowered blood pressure in sodium-deficient dogs, with in vivo potency 19 times that shown by 1, in close agreement with the relative in vitro potencies.Structure-activity results are presented that show the minimal N-terminus for these inhibitors.An ACHPA-containing pentapeptide, N--L-phenylalanyl-L-histydyl-ACHPA-L-lecyl-L-phenylalanyl amide , retained subnanomolar inhibitory potency.Molecular modelling studies are described that suggested the design of ACHPA.