Cbz-aspartic acid (tert-butyl ester) | 3588-56-5

• 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: Cbz-aspartic acid (tert-butyl ester)
• 英文别名: N-[(phenylmethoxy)carbonyl]-D-aspartic acid,1,1-dimethylethyl ester；2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester；Z-aspartic acid 4-tert-butyl ester；carbobenzyloxy-L-aspartic acid-beta-tert-butyl ester；N-benzyloxycarbonyl-β-tert-butyl-aspartic acid；4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 3588-56-5
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: HLSLRFBLVZUVIE-UHFFFAOYSA-N

物化性质

• 沸点：
  513.1±50.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Cbz-aspartic acid (tert-butyl ester) 在 N-甲基吗啉 、 sodium tetrahydroborate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (RS)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Enantiomeric Purity of Protectedα-Amino and Peptide Aldehydes

  摘要：

  The synthesis of enantiomerically pure Ac-Tyr-Val-Ala-Asp(O'Bu)-H dimethyl acetal ((S)-1) is reported, a protected tetrapeptide C-terminal aldehyde belonging to a class of potent, reversible inhibitors of cysteine proteases (e.g.. interleukin-1 beta-converting enzyme (ICE), also called caspase-1). The coupling of the precursors Ac-Tyr-Val-Ala-OH ((S)-8) and H-Asp(O'Bu)-H dimethyl acetal ((S)-6) gave (S)-1 in a yield of 85%, with epimerization of < 2% at the alanine and aspartic-acid residue. (S)-6 itself was synthesized in four steps in an overall yield of 83% with an ee >98%.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1960::aid-hlca1960>3.0.co;2-2
• 作为产物：
  描述：

  N-<(phenylmethoxy)carbonyl>-D-aspartic acid, 1-(1,1-dimethylethyl) 4-methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 Cbz-aspartic acid (tert-butyl ester)
  参考文献：
  名称：

  Aminobutanoic acid compounds having metalloprotease inhibiting properties

  摘要：

  以下化学式（I）的氨基丁酸：##STR1##其中R.sup.1 -R.sup.5是各种取代基，新颖的中间体，用于治疗炎症性疾病、脱髓鞘性疾病和肿瘤转移的药物组合物，用于此类治疗的方法以及制备化合物的过程（I）。

  公开号：

  US05326760A1

文献信息

• C-terminal modified oxamyl dipeptides as inhibitors of the ICE-ced-3 family of cysteine proteases
  申请人：——

  公开号：US20020042376A1

  公开（公告）日：2002-04-11

  This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as to the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  这项发明涉及新型的oxamyl二肽ICE/ced-3家族抑制剂化合物。该发明还涉及含有这些化合物的药物组合物，以及在治疗患有炎症性、自身免疫和神经退行性疾病的患者中使用这些组合物，用于预防缺血性损伤，并用于保存即将进行移植手术的器官。
• [EN] PYRIDAZINE DERIVATIVES AS FACTOR XIA INHIBITORS<br/>[FR] DÉRIVÉS DE LA PYRIDAZINE INHIBITEURS DU FACTEUR XIA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2009114677A1

  公开（公告）日：2009-09-17

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein the variables A, L1, L2, R2, R11, and M are as defined herein. These compounds are selective factor XIa inhibitors or dual inhibitors of fXIa and plasma kallikrein. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating thromboembolic and/or inflammatory disorders using the same.

  本发明提供了式（I）的化合物：或其立体异构体、互变异构体或药学上可接受的盐，其中变量A、L1、L2、R2、R11和M如本文所定义。这些化合物是选择性因子XIa抑制剂或fXIa和血浆激肽原的双重抑制剂。本发明还涉及包含这些化合物的药物组合物以及使用它们治疗血栓栓塞和/或炎症性疾病的方法。
• Pyridazine and pyridazinone derivatives as potent and selective factor XIa inhibitors
  作者：Zilun Hu、Cailan Wang、Wei Han、Karen A. Rossi、Jeffrey M. Bozarth、Yiming Wu、Steven Sheriff、Joseph E. Myers、Joseph M. Luettgen、Dietmar A. Seiffert、Ruth R. Wexler、Mimi L. Quan

  DOI：10.1016/j.bmcl.2018.02.049

  日期：2018.4

  Pyridazine and pyridazinone derivatives were designed and synthesized as coagulation factor XIa inhibitors. Potent and selective inhibitors with single digit nanomolar affinity for factor XIa were discovered. Selected inhibitors demonstrated moderate oral bioavailability.

  设计并合成了哒嗪和哒嗪酮衍生物作为凝血因子XIa抑制剂。已发现对因子XIa具有一位数纳摩尔亲和力的强效和选择性抑制剂。选定的抑制剂表现出中等的口服生物利用度。
• Thiazole derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06344562B1

  公开（公告）日：2002-02-05

  Compounds of the formula: as well as pharmaceutically usable salts and esters thereof, wherein R1, R2 and R3 have the significance ascribed herein, inhibit binding of adhesive proteins to the surface of different types of cell and accordingly influence cell-cell and cell-matrix interactions. These compounds can be used in the form of pharmaceutical preparations for the control or prevention of neoplasms, tumor metastasing, tumor growth, osteoporosis, Paget's disease, diabetic retinopathy, macular degeneration, restenosis following vascular intervention, psoriasis, arthritis, fibrosis, kidney failure, as well as infection caused by viruses, bacteria or fungi.

  该公式的化合物：以及其药用盐和酯，其中R1、R2和R3具有在此规定的意义，抑制粘附蛋白质与不同类型细胞表面的结合，从而影响细胞-细胞和细胞-基质相互作用。这些化合物可以用作制药制剂的形式，用于控制或预防肿瘤、肿瘤转移、肿瘤生长、骨质疏松症、帕盖特病、糖尿病视网膜病变、黄斑变性、血管介入后再狭窄、银屑病、关节炎、纤维化、肾功能衰竭，以及由病毒、细菌或真菌引起的感染。
• PRODRUGS OF CYTOTOXIC ACTIVE AGENTS HAVING ENZYMATICALLY CLEAVABLE GROUPS
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20190077752A1

  公开（公告）日：2019-03-14

  The invention relates to novel prodrugs or conjugates of the general formula (Ia) in which cytotoxic drugs, for example kinesin spindle protein inhibitors, are masked with legumain-cleavable groups and hence release the drug, and to the use of these prodrugs or conjugates for treatment and/or prevention of diseases, and to the use of these prodrugs or conjugates for production of medicaments for treatment and/or prevention of diseases, especially of hyperproliferative and/or angiogenic disorders, for example cancers.

  该发明涉及通式(Ia)的新型前药或结合物，其中细胞毒性药物，例如动力蛋白抑制剂，被腿蛋白酶可切割基团掩蔽，从而释放药物，并且涉及使用这些前药或结合物用于治疗和/或预防疾病，以及使用这些前药或结合物用于生产用于治疗和/或预防疾病的药物，特别是治疗和/或预防高增殖和/或血管生成异常的疾病，例如癌症。