(3S)-3-iso-propyl-1-p-methoxybenzyl-piperazine-2,5-dione | 479681-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S)-3-iso-propyl-1-p-methoxybenzyl-piperazine-2,5-dione
• 英文别名: (S)-N(1)-(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione；(3S)-1-[(4-methoxyphenyl)methyl]-3-propan-2-ylpiperazine-2,5-dione
• CAS: 479681-20-4
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: OTTXXQGNSVYQBE-AWEZNQCLSA-N

物化性质

• 熔点：
  145 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  530.1±50.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-iso-propyl-1-p-methoxybenzyl-piperazine-2,5-dione 在 ammonium cerium(IV) nitrate 、 地昔帕明 、 三丁基膦 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 107.64h， 生成 (+)-(5aR,8S,15bR,16aR)-8-iso-propyl-5,5a,8,15b,16,16a-hexahydro-indolo[3'',2''-4',5']pyrrolo[2',1'-3,4]pyrazino[2,1-b]quinazoline-7,10-dione
  参考文献：
  名称：

  Influence of N(2)-substitution in the alkylation of (4S)-alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

  摘要：

  1-Alkylation of O(3)-lactim, N(11)-azaenolate dilithium species derived from N(2)-H compounds 1a and 1b and the lithium azaenolates derived from the N(2)-phenyl and N(2)-(1-arylethyl) substituted compounds 2, 3 and 4 is studied. In 1 the trans-diastereoselectivity of 1-alkylation is controlled by 1,4-asyrnmetric induction, with some of these products prect.rsors of the ent-ardeemin framework. By contrast in compounds 2-4, the stabilization of the lithium azaenolate imposed by the phenyl substituent in 2, and the repulsive steric 1,2- interactions present in the initially formed 1,4-trans derivatives of 3 and 4, favou a C(1)-epimerization to the 1,4-cis isomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.034
• 作为产物：
  描述：

  L-缬氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 (3S)-3-iso-propyl-1-p-methoxybenzyl-piperazine-2,5-dione
  参考文献：
  名称：

  关于二酮哌嗪烯醇酯烷基化中非对映选择性的起源

  摘要：

  高水平 非对映选择性 观察到烯醇锂的苄基化 （小号） - ñ，Ñ ' -双-对甲氧基苄基-3-异丙基-哌嗪-2,5-二酮， （小号） - Ñ（1） -对-methoxybenzyl- Ñ（4） -甲基-3-异丙基-哌嗪-2,5-二酮 和 （小号） - Ñ（1） -甲基- Ñ（4） -对甲氧基苄基-3-异丙基-哌嗪-2,5-二酮。这些数据表明，对于这些二酮哌嗪的烷基化模板观察到的高选择性diastereofacial主要的立体化学信息从C（3）到C（6）中继的结果经由1,2-扭转应变的由引入的影响Ñ -烷基取代基，而不是仅通过最小化空间相互作用来实现。

  DOI：

  10.1039/b701628j

文献信息

• [EN] INHIBITORS OF THE BCL6 BTB DOMAIN PROTEIN-PROTEIN INTERACTION AND USES THEREOF<br/>[FR] INHIBITEURS DE L'INTERACTION PROTÉINE-PROTÉINE DU DOMAINE BCL6 BTB ET LEURS UTILISATIONS
  申请人：ONTARIO INSTITUTE FOR CANCER RES OICR

  公开号：WO2019153080A1

  公开（公告）日：2019-08-15

  The present application relates to compounds of Formula I (I) or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, to compositions comprising these compounds or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, and various uses in the treatment of diseases, disorders or conditions that are treatable by inhibiting interactions with BCL6 BTB, such as cancer.

  本申请涉及公式I（I）化合物或其药用可接受的盐、溶剂化合物和/或前药，包括含有这些化合物或药用可接受的盐、溶剂化合物和/或前药的组合物，以及在治疗可通过抑制与BCL6 BTB的相互作用可治疗的疾病、紊乱或状况中的各种用途，如癌症。
• Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates
  作者：Stephen G. Davies、A. Christopher Garner、Jaqueline V. A. Ouzman、Paul M. Roberts、Andrew D. Smith、Emma J. Snow、James E. Thomson、Juan A. Tamayo、Richard J. Vickers

  DOI：10.1039/b704475e

  日期：——

  Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

  (S)-N(1)-甲基-5-甲氧基-6-异丙基-3,6-二氢吡嗪-2-酮和(S)-N(1)-对甲氧基苄基-5-甲氧基-6-异丙基-3,6-二氢吡嗪-2-酮的顺序对映体烷基化反应以极好的非对映选择性（>90% de）进行，以高对映体过量（>90% de）得到季δ-氨基酸、6- 二氢嗪-2-酮的非对映选择性极佳（de>90%），在脱保护和水解后可得到对映体过量（ee>98%）的季δ-氨基酸。
• Substituted heteroaryls as inhibitors of the BCL6 BTB domain protein-protein interaction
  申请人：Ontario Institute for Cancer Research (OICR)

  公开号：US11518764B2

  公开（公告）日：2022-12-06

  The present application relates to compounds of Formula I or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, to compositions comprising these compounds or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, and various uses in the treatment of diseases, disorders or conditions that are treatable by inhibiting interactions with BCL6 BTB, such as cancer.

  本申请涉及式 I 化合物 或其药学上可接受的盐、溶液剂和/或原药，涉及包含这些化合物或其药学上可接受的盐、溶液剂和/或原药的组合物，以及在治疗可通过抑制与 BCL6 BTB 的相互作用来治疗的疾病、失调或病症（如癌症）中的各种用途。
• Homochiral Supramolecular Polymerization of an “<i>S</i>”-Shaped Chiral Monomer:  Translation of Optical Purity into Molecular Weight Distribution
  作者：Yasuhiro Ishida、Takuzo Aida

  DOI：10.1021/ja028403h

  日期：2002.11.1

  An "S"-shaped chiral motif of a p-xylylene-bridged bis(cyclic dipeptide) (1), having four hydrogen-bonding amide functionalities, formed a homochiral supramolecular polymer in solution. X-ray crystallography of a slightly modified version of 1 for an enhanced crystallinity showed one-dimensional columnar assemblies via four double hydrogen-bonding interactions. Model studies with half-protected analogues of 1 indicated a nearly perfect enantioselectivity in hydrogen-bonding dimerization. When 1 was not racemic but enriched in either of the enantiomers, a supramolecular polymer with a bimodal molecular weight distribution resulted, due to the formation of two homochiral polymers with different molecular weights. By taking advantage of this, separation of optically pure 1 from an enantiomerically unbalanced mixture was possible by means of size-exclusion chromatography.
• INHIBITORS OF THE BCL6 BTB DOMAIN PROTEIN-PROTEIN INTERACTION AND USES THEREOF
  申请人：Ontario Institute for Cancer Research (OICR)

  公开号：US20200331921A1

  公开（公告）日：2020-10-22

  The present application relates to compounds of Formula I (I) or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, to compositions comprising these compounds or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, and various uses in the treatment of diseases, disorders or conditions that are treatable by inhibiting interactions with BCL6 BTB, such as cancer.