Ueda, Satoshi et al. published their research in Journal of Medicinal Chemistry in 2007 | CAS: 86069-86-5

Structure-Activity Relationships of Cyclic Peptide-Based Chemokine Receptor CXCR4 Antagonists: Disclosing the Importance of Side-Chain and Backbone Functionalities was written by Ueda, Satoshi;Oishi, Shinya;Wang, Zi-xuan;Araki, Takanobu;Tamamura, Hirokazu;Cluzeau, Jerome;Ohno, Hiroaki;Kusano, Shuichi;Nakashima, Hideki;Trent, John O.;Peiper, Stephen C.;Fujii, Nobutaka. And the article was included in Journal of Medicinal Chemistry in 2007.Formula: C21H21NO4 The following contents are mentioned in the article:

Previously, we have identified a highly potent CXCR4 antagonist 2 [cyclo(-D-Tyr¹-Arg²-Arg³-Nal⁴-Gly⁵-)] and its Arg² epimer 3 [cyclo(-D-Tyr¹–D-Arg²-Arg³-Nal⁴-Gly⁵-)] by the screening of cyclic pentapeptide libraries that were designed based on the structure-activity relationship studies on 14-residue peptidic CXCR4 antagonist 1. In the present study, a new series of analogs of 2 and 3 were synthesized to evaluate the influences of peptide side-chain and backbone modification on bioactivities. Based on the Ala-scanning study, in which each residue in 2 and 3 was replaced with Ala having the identical chirality, substitution of Arg³ and Nal⁴ [Nal = L-3-(2-naphthyl)alanine] with Ala (compounds 6, 7, 10, 11) led to significant loss of the potency, indicating these amino acids are more important contributors to the bioactivity. For the cyclic peptide backbone, several modifications including D/L-Ala or cyclic amino acids substitution at the Gly⁵ position and sequential N-methylation on amide nitrogens were conducted. Among the analogs, compounds 13 [cyclo(-D-Tyr¹-Arg²-Arg³-Nal⁴–D-Ala⁵-)] and 32 [cyclo(-D-Tyr¹–D-MeArg²-Arg³-Nal⁴-Gly⁵-)] were close in potency to the most potent lead 2. NMR and conformational anal. indicated that both of these analogs favor the same backbone conformation as 2, whereas similar anal. of less potent analogs indicates that an altered backbone conformation is favored. The conformational anal. showed that steric repulsion by a 1,3-allylic strain-like effect across the planar peptide bond might contribute to the conformational preferences of cyclic pentapeptides. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Formula: C21H21NO4).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Formula: C21H21NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem