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3-(N-1-Trityl-imidazol-4-yl)propionic Acid is a white solid intermediate compound that plays a significant role in the synthesis of various pharmaceutical agents. It is characterized by its trityl-imidazol structure, which contributes to its unique chemical properties and potential applications in the field of medicinal chemistry.

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  • 160446-35-5 Structure
  • Basic information

    1. Product Name: 3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID
    2. Synonyms: 3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID;DEAMINO-HIS(TRT)-OH;N-1-TRITYL-DEAMINO-HISTIDINE;N-1-TRITYL-DIHYDROUROCANIC ACID;N-1-Trityl-deamino-histidine, (3-(N-1-Trityl-imidazol-4-yl)propionic acid, N-1-Trityl-dihydrourocanic acid;N-1-Tr;N-1-Trityl-dihydrourocanic acid, 3-(N-1-Trityl-iMidazol-4-yl)propionic acid;3-(1-Trityl-1H-iMidazol-4-yl)propanoic acid
    3. CAS NO:160446-35-5
    4. Molecular Formula: C25H22N2O2
    5. Molecular Weight: 382.45
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 160446-35-5.mol
  • Chemical Properties

    1. Melting Point: 185℃ (ethyl acetate tetrahydrofuran )
    2. Boiling Point: 562.8±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.13±0.1 g/cm3 (20 ºC 760 Torr)
    6. Refractive Index: N/A
    7. Storage Temp.: -15°C
    8. Solubility: Chloroform (Slightly)
    9. PKA: 3.94±0.10(Predicted)
    10. CAS DataBase Reference: 3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID(CAS DataBase Reference)
    11. NIST Chemistry Reference: 3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID(160446-35-5)
    12. EPA Substance Registry System: 3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID(160446-35-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 160446-35-5(Hazardous Substances Data)

160446-35-5 Usage

Uses

Used in Pharmaceutical Industry:
3-(N-1-Trityl-imidazol-4-yl)propionic Acid is used as an intermediate for the preparation of imidazole-containing tetrahydrobenzodiazepine inhibitors of farnesyltransferase. These inhibitors are essential in the development of drugs targeting the enzyme farnesyltransferase, which is involved in the post-translational modification of proteins and has been implicated in various diseases, including cancer.
3-(N-1-Trityl-imidazol-4-yl)propionic Acid is also used in the synthesis of nonracemic arylpiperazinone analogs of the carboxyl-terminal CAAL sequence of protein geranylgeranyltransferase-I (PGGTase-I). These analogs serve as selective inhibitors of PGGTase-I and protein farnesyltransferase, both of which are key enzymes in the post-translational prenylation of proteins. Inhibition of these enzymes has potential therapeutic applications in the treatment of various diseases, including cancer and neurodegenerative disorders.

Check Digit Verification of cas no

The CAS Registry Mumber 160446-35-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,0,4,4 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 160446-35:
(8*1)+(7*6)+(6*0)+(5*4)+(4*4)+(3*6)+(2*3)+(1*5)=115
115 % 10 = 5
So 160446-35-5 is a valid CAS Registry Number.

160446-35-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(1-tritylimidazol-4-yl)propanoic acid

1.2 Other means of identification

Product number -
Other names Deamino-His(Trt)-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:160446-35-5 SDS

160446-35-5Relevant articles and documents

STABLE GLP-1 BASED GLP-1/GLUCAGON RECEPTOR CO-AGONISTS

-

Page/Page column 38; 39, (2016/05/02)

The application concerns stable and protracted GLP-1 derivatives which are GLP-l/glucagon receptor co-agonists, compositions thereof, use of the GLP-1 derivatives in medicine, and to methods of treatment comprising administration of the GLP-1 derivatives

Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists

Ghorai, Prasanta,Kraus, Anja,Keller, Max,G?tte, Carsten,Igel, Patrick,Schneider, Erich,Schnell, David,Bernhardt, Günther,Dove, Stefan,Zabel, Manfred,Elz, Sigurd,Seifert, Roland,Buschauer, Armin

supporting information; experimental part, p. 7193 - 7204 (2009/10/02)

N1-Aryl(heteroaryl)alkyl-N2-[3-(1H-imidazol-4-yl) propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of magnitude. Some acylguanidines with one phenyl ring were even more potent than their diaryl analogues. As demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor subtype selectivity depends on the imidazolylpropylguanidine moiety (privileged structure), opening an avenue to distinct pharmacological tools including potent H4R agonists.

Preparation of protected β2- and β3- homocysteine, β2- and β3-homohistidine, and β2-homoserine for solid-phase syntheses

Lelais, Gerald,Micuch, Peter,Josien-Lefebvre, Delphine,Rossi, Francesco,Seebach, Dieter

, p. 3131 - 3159 (2007/10/03)

The Ser, Cys, and His side chains play decisive roles in the syntheses, structures, and functions of proteins and enzymes. For our structural and biomedical investigations of β-peptides consisting of amino acids with proteinogenic side chains, we needed to have reliable preparative access to the title compounds. The two β3-homoamino acid derivatives were obtained by Arndt-Eistert methodology from Boc-His(Ts)-OH and Fmoc-Cys(PMB)-OH (Schemes 2-4), with the side-chain functional groups' reactivities requiring special precautions. The β2-homoamino acids were prepared with the help of the chiral oxazolidinone auxiliary DIOZ by diastereoselective aldol additions of suitable Ti-enolates to formaldehyde (generated in situ from trioxane) and subsequent functional-group manipulations. These include OH → OtBu etherification (for β2hSer; Schemes 5 and 6), OH → STrt replacement (for β2hCys; Scheme 7), and CH 2OH → CH2N3 → CH2NH 2 transformations (for β2hHis; Schemes 9-11). Including protection/deprotection/re-protection reactions, it takes up to ten steps to obtain the enantiomerically pure target compounds from commercial precursors. Unsuccessful approaches, pitfalls, and optimization procedures are also discussed. The final products and the intermediate compounds are fully characterized by retention times (tR), melting points, optical rotations, HPLC on chiral columns, IR, 1H- and 13C-NMR spectroscopy, mass spectrometry, elemental analyses, and (in some cases) by X-ray crystal-structure analysis.

Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them

-

, (2008/06/13)

Compounds of the formula (I), or a pharmaceutically-acceptable salt, or an in-vivo-hydrolysable ester thereof, wherein, for example, X is —O— or —S—; HET is an optionally substituted C-linked 5-membered heteroaryl ring containing 2 to 4 heteroatoms independently selected from N, O and S; Q is selected from, for example, Q1 and Q2 R2 and R3 are independently hydrogen or fluoro; T is selected from a range of groups, for example, an N-linked (fully unsaturated) 5-membered heteroaryl ring system or a group of formula (TC5): wherein Rc is, for example, R13CO—, R13SO2— or R13CS—; wherein R13 is, for example, optionally substituted (1-10C)alkyl or R14C(O)O(1-6C)alkyl wherein R14 is optionally substituted (1-10C)alkyl; are useful as antibacterial agents; and processes for their manufacture and pharmaceutical compositions containing them are described.

Nα-Imidazolylalkyl and Pyridylalkyl Derivatives of Histaprodifen: Synthesis and in Vitro Evaluation of Highly Potent Histamine H1-Receptor Agonists

Menghin, Sonja,Pertz, Heinz H.,Kramer, Kai,Seifert, Roland,Schunack, Walter,Elz, Sigurd

, p. 5458 - 5470 (2007/10/03)

A novel series of Nα-imidazolylalkyl and pyridylalkyl derivatives of histaprodifen (6, 2-[2-(3,3-diphenylpropyl)imidazol-4-yl]ethanamine) was synthesized and evaluated as histamine H1-receptor agonists. The title compounds displayed partial agonism at contractile H1-receptors of guinea pig ileum and were at least equipotent with histamine. Agonist effects of the new derivatives were susceptible to blockade by the H1-receptor antagonist mepyramine (2-100 nM). In the imidazole series, suprahistaprodifen (51, [2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl]-[2-(1H-imidazol-4-yl) ethyl]amine, Nα-2-[(1H-imidazol-4-yl)ethyl]histaprodifen) showed the highest H1-receptor agonist potency ever reported in the literature (pEC50 8.26, efficacy Emax 96%). Elongation of the alkyl spacer from ethyl to butyl decreased activity from 3630% (ethyl, 51) to 163% (butyl, 53) of histamine potency. The exchange of the terminal imidazole nucleus for a pyridine ring resulted in compounds with comparably high potency. A decrease in agonist potency and efficacy was observed when the attachment of the alkyl spacer was consecutively changed from the ortho to the meta and the para position, respectively, of the pyridine ring. The pyridine series that contained a butyl chain possessed the highest potency and affinity. Nα-[4-(2-pyridyl)butyl]histaprodifen (56) emerged as a strong partial agonist, being almost equipotent with 51 (pEC50 8.16, E max 89%). Compounds 51 and 56 also showed potent partial agonism at contractile H1 receptors in guinea pig aorta and potently activated H1-receptor-mediated endothelium-dependent relaxation in the rat aorta. Compounds 51-65 displayed low to moderate affinity at H2, H3, and M3 receptors in functional models of guinea pig. Collectively, Nα-imidazolylalkyl- and Nα -pyridylalkyl-substituted histaprodifens represent a novel class of potent H1-receptor agonists. These compounds may be useful to define the (patho)physiological role of the H1-receptor and refine molecular models of H1-receptor activation.

Inhibitors of protein isoprenyl transferases

-

, (2008/06/13)

Compounds having the formula or a pharmaceutically acceptable salt thereof wherein R1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L2—, and (i) heterocyclic-L2—; R2 is selected from (a) (b) —C(O)NH—CH(R14)—C(O)OR15, (c) (d) —C(O)NH—CH(R14)—C(O)NHSO2R16 (e) —C(O)NH—CH(R14)-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R14)—C(O)NR17R18; R3 is heterocyclic, aryl, substituted or unsubstituted cycloalkyl; R4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L1 is absent or is selected from (a) —L4—N(R5)—L5—, (b) —L4—O—L5—, (c) —L4—S(O)n—L5— (d) —L4-L6—C(W)—N(R5)—L5—, (e) —L4-L6—S(O)m—N(R5)—L5—, (f) —L4—N(R5)—C(W)—L7-L5—, (g) —L4—N(R5)—S(O)p—L7—L5—, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, and (j) optionally substituted alkynylene are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

Novel small renin inhibitors containing 4,5- or 3,5-Dihydroxy-2-substituted-6-phenylhexanamide replacements at the P2-P3 sites

Jung, Grace L.,Anderson, Paul C.,Bailey, Murray,Baillet, Monique,Bantle, Gary W.,Berthiaume, Sylvie,Lavallee, Pierre,Llinas-Brunet, Montse,Thavonekham, Bounkham,Thibeault, Diane,Simoneau, Bruno

, p. 2317 - 2336 (2007/10/03)

Renin inhibitors containing a 4,5- or a 3,5-dihydroxy-2-substituted-6-phenylhexanamide fragment at the P2-P3 sites have been prepared and evaluated. The four possible diastereomeric diols of the two series of inhibitors were synthesi

5-amino-4-hydroxyhexanoic acid derivatives

-

, (2008/06/13)

Compounds of formula I STR1 or their hydroxy-protected derivatives, and compounds of formula I' STR2 wherein T is an acyl radical of formula Z STR3 wherein Rz is unsubstituted or substituted hydrocarbyl wherein at least one carbon atom has been replaced by a hetero atom with the proviso that a hetero atom is not bonded directly to the carbonyl to which the radical Rz is bonded, alkyl having two or more carbon atoms, lower alkenyl, lower alkynyl, aryl or unsubstituted or substituted amino, and wherein the radicals R1, B1, R2, R3, A1, A2 and NR4 R5 are as defined in the description, and precursors thereof, are described. The compounds have pharmaceutical activity, for example in the treatment of retroviral diseases, such as AIDS.

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