N-benzyloxycarbonyl-phenylalanine amide | 53562-23-5

• 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: N-benzyloxycarbonyl-phenylalanine amide
• 英文别名: N-Benzyloxycarbonyl-phenylalanin-amid；(2-Phenyl-1-carbamoyl-aethyl)-carbamidsaeure-benzylester；N-[(benzyloxy)carbonyl]phenylalaninamide；carbobenzoxy-L-phenylalanineamide；Z-DL-Phe-NH2；benzyl N-(1-carbamoyl-2-phenylethyl)carbamate；benzyl N-(1-amino-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS: 53562-23-5
• 化学式: C₁₇H₁₈N₂O₃
• mdl: MFCD00731964
• 分子量: 298.342
• InChiKey: HHBOFAIEPRHUSR-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  549.4±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-phenylalanine amide 在 硫化氢 作用下， 生成 Z-DL-Phenylalanin-thiono-ethylester
  参考文献：
  名称：

  Ried,W.; Schmidt,E., Justus Liebigs Annalen der Chemie, 1966, vol. 695, p. 217 - 225

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-苯丙氨酸 在 ammonium hydroxide 、 氯甲酸乙酯 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 N-benzyloxycarbonyl-phenylalanine amide
  参考文献：
  名称：

  通过锌介导的α-氨基酸同系物立体选择性进入功能化的1,2-二胺。

  摘要：

  已经开发了由α-氨基酸进行的一般的立体选择性合成4,5-二取代的咪唑烷-2-酮的方法：关键步骤是溴乙酸在α-氨基腈上的布莱斯反应，并进一步还原。尽管用氰基硼氢化钠还原得到具有中等到良好的立体选择性的顺式和反式异构体6a-e的混合物，但是用液氨中的钠还原得到具有完全立体选择性的反式异构体8a-e。尿素的酸性水解得到4-氨基-吡咯烷酮，其可以是β，γ-二氨基酸或3-氨基吡咯烷的前体。

  DOI：

  10.1021/ol0708020

文献信息

• Phenylalanine derivatives enhancing intestinal absorption of insulin in mice.
  作者：YUSUKE AMINO、KAZUHIRO KAWADA、KOJI TOI、IZUMI KUMASHIRO、KOJI FUKUSHIMA

  DOI：10.1248/cpb.36.4426

  日期：——

  The adjuvant effect of N-acyl-L-and D-phenylalanine derivatives on intestinal absorption of insulin was investigated in normal mice. The correlation between the chemical structural properties of the N-acyl moiety and the absorption-promoting activity was estimated from the glucose concentrations and the insulin levels in the blood of mice after oral combined administration of insulin and adjuvant. The chemical structural properties of N-acyl-phenylalanine derivatives necessary for adjuvant effect on intestinal absorption of insulin were as follows. 1. An aromatic ring is present, separated by two atoms from the acyl carbonyl group. 2. Either of X or Y is oxygen or X-Y is a double bond in Fig.2. 3. The N-acyl moiety has small hydrophobic substituents, such as F, Cl, or Me at Rα, Rβ, Rη and has an appropriate hydrophilic-hydrophobic balance of the overall molecule. The use of these agents to enhance insulin absorption offers the possibility of a new approach to oral insulin therapy.

  研究了N-酰基-L-和D-苯丙氨酸衍生物对正常小鼠胰岛素肠道吸收的辅助效应。根据小鼠口服胰岛素和辅料联合给药后的血糖浓度和胰岛素水平，推测了N-酰基部分的化学结构性质与促吸收活性之间的相关性。N-酰基-苯丙氨酸衍生物对胰岛素肠道吸收具有辅效应的化学结构性质如下：1. 芳环存在，与酰基羰基相隔两个原子。2. 图2中的X或Y之一为氧，或者X-Y是双键。3. N-酰基部分具有较小的疏水取代基，如F、Cl或Me在Rα、Rβ、Rη位置，并且整个分子具有适当的亲水-疏水平衡。利用这些制剂增强胰岛素吸收，为口服胰岛素治疗提供了新的途径。
• [EN] PHENYL OR HETEROARYL AMINO ALKANE DERIVATIVES AS IP RECEPTOR ANTAGONIST<br/>[FR] DERIVES DE PHENYL- OU HETEROARYLAMINO-ALCANES COMME ANTAGONISTES DU RECEPTEUR IP
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004043926A1

  公开（公告）日：2004-05-27

  The present invention relates to a phenyl or heteroaryl amino alkane derivatives which are useful as an active ingredient of pharmaceutical preparations. The phenyl or heteroaryl amino alkanes of the present invention have IP receptor antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with IP receptor antagonistic activity. Such diseases include urological diseases or disorder as follows: bladder outlet obstruction, overactive bladder, urinary incontinence, detrusor hyper-reflexia, detrusor instability, reduced bladder capacity, frequency of micturition, urge incontinence, stress incontinence, bladder hyperreactivity, benighn prostatic hypertrophy (BPH), prostatitis, urinary frequency, nocturia, urinary urgency, pelvic hypersensitivity, urethritis, pelvic pain syndrome, prostatodynia, cystitis, or idiophatic bladder hypersensitivity. The compounds of the present invention are also useful for treatment of pain including, but not limited to inflammatory pain, neuropathic pain, acute pain, chronic pain, dental pain, premenstrual pain, visceral pain, headaches, and the like; hypotension; hemophilia and hemorrhage; and inflammation, since the diseases also is alleviated by treatment with an IP receptor antagonist.

  本发明涉及一种苯基或杂环烷基氨基烷衍生物，其作为药物制剂的活性成分是有用的。本发明的苯基或杂环烷基氨基烷具有IP受体拮抗活性，并可用于预防和治疗与IP受体拮抗活性相关的疾病。这些疾病包括泌尿系统疾病或障碍，如：膀胱出口梗阻、膀胱过度活跃、尿失禁、膀胱逼尿肌过度反射、膀胱逼尿肌不稳定、膀胱容量减少、排尿频率增加、急迫性尿失禁、压力性尿失禁、膀胱高反应性、良性前列腺增生（BPH）、前列腺炎、尿频、夜尿频、尿急、盆腔过敏、尿道炎、盆腔疼痛综合征、前列腺疼痛综合征、膀胱炎或特发性膀胱过敏。本发明的化合物还可用于治疗疼痛，包括但不限于炎症性疼痛、神经病性疼痛、急性疼痛、慢性疼痛、牙痛、经前疼痛、内脏疼痛、头痛等；低血压；血友病和出血；以及炎症，因为这些疾病也可以通过IP受体拮抗剂治疗而得到缓解。
• Imaging of protease activity in live cells using activity based probes
  申请人：Bogyo S. Matthew

  公开号：US20070036725A1

  公开（公告）日：2007-02-15

  Methods and materials for the imaging of cells containing active proteases such as cathepsin are disclosed. The present materials include activity based probes that bind to an enzyme and are subsequently cleaved. Cleavage results in a fluorescent signal due to removal of a quenching group which, when present on the probe causes altered or no fluorescence. The probes employ an acyloxymethyl ketone reactive group, one or more amino acids for determining specificity, a fluorophore and a quencher. The probes are cell permeable and may use, for example, a QSY7 (diarylyrhodamine) quencher and a BODIPY (bora-diaza-indecene) dye.

  揭示了用于成像含有活性蛋白酶（如半胱氨酸蛋白酶）的细胞的方法和材料。目前的材料包括结合到酶并随后被切割的活性基团探针。切割导致荧光信号的产生，因为去除了一个熄灭基团，当存在于探针上时，会导致改变或无荧光。这些探针使用酰氧甲基酮反应基团，一个或多个氨基酸用于确定特异性，一个荧光团和一个熄灭剂。这些探针具有细胞穿透性，例如，可以使用QSY7（二芳基罗丹明）熄灭剂和BODIPY（硼二氮杂环庚烯）染料。
• Phenylalanine-glycine compounds having anti-tumor activity, process for
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：US05411964A1

  公开（公告）日：1995-05-02

  A phenylalanine-glycine compound of formula (I): ##STR1## wherein R represents a residue of an antitumor substance, or a salt or ester thereof, a process for preparation thereof, and a pharmaceutical composition containing the same are described. The novel conjugate of the phenylalanine-glycine compound and the antitumor substance exhibits superior antitumor activity in comparison with the case wherein an antitumor substance is administered alone or as a mixture with phenylalanine.

  一种苯丙氨酸-甘氨酸化合物的化学式(I)：##STR1##其中R代表抗肿瘤物质的残基，或其盐或酯，描述了其制备方法以及含有该化合物的药物组合物。苯丙氨酸-甘氨酸化合物与抗肿瘤物质的新型结合物在抗肿瘤活性方面表现出优越性，与单独给予抗肿瘤物质或与苯丙氨酸混合的情况相比。
• Renin inhibitors
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0376012A2

  公开（公告）日：1990-07-04

  The invention is new renin inhibitor depeptide and tripeptide derivatives of the formula:

  本发明是式中的新型肾素抑制剂二肽和三肽衍生物：