N^α-Boc-m-amino-D,L-phenylglycine | 54895-26-0

• 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^α-Boc-m-amino-D,L-phenylglycine
• 英文别名: N-Boc-DL-3-aminophenylglycine；alpha-t-Butoxycarbonylamino-m-aminophenylacetic acid；2-(3-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 54895-26-0
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: PCTNHJKMUWYKHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-Boc-m-amino-D,L-phenylglycine 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-Amino-2-[3-(diaminomethylideneamino)phenyl]acetic acid
  参考文献：
  名称：

  Conformationally-restricted arginine analogues as alternative substrates and inhibitors of nitric oxide synthases

  摘要：

  Conformationally restricted arginine analogues (1-5) were synthesized and found to be alternative substrates or inhibitors of the three isozymes of nitric oxide synthase (NOS). A comparison of k(cat)/K-m values shows that (E)-3,4-didehydro-D,L-arginine(1) is a much better substrate than the corresponding (Z)-isomer (2) and 3-guanidino-D,L-phenylglycine (3), although none is as good a substrate as is arginine; 5-keto-D,L-arginine (4) is not a substrate, but is an inhibitor of the three isozymes. Therefore, it appears that arginine binds to all of the NOS isozymes in an extended (E-like) conformation. None of the compounds exhibits time-dependent inhibition of NOS, but they are competitive reversible inhibitors. Based on the earlier report that NW-propyl-L-arginine is a highly selective nNOS inhibitor (Zhang, H. Q.; Fast, W.; Marletta, M.; Martasek, P.; Silverman, R. B. J. Med. Chem. 1997, 40, 3869), (E)-N-omega-propyl-3,4-didehydro-D,L-arginine (5) was synthesized, but it was shown to be weakly potent and only a mildly selective inhibitor of NOS. Imposing conformational rigidity on an arginine backbone does not appear to be a favorable approach for selective NOS inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00029-2
• 作为产物：
  描述：

  氨基-(3-硝基-苯基)-乙酸 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N^α-Boc-m-amino-D,L-phenylglycine
  参考文献：
  名称：

  Conformationally-restricted arginine analogues as alternative substrates and inhibitors of nitric oxide synthases

  摘要：

  Conformationally restricted arginine analogues (1-5) were synthesized and found to be alternative substrates or inhibitors of the three isozymes of nitric oxide synthase (NOS). A comparison of k(cat)/K-m values shows that (E)-3,4-didehydro-D,L-arginine(1) is a much better substrate than the corresponding (Z)-isomer (2) and 3-guanidino-D,L-phenylglycine (3), although none is as good a substrate as is arginine; 5-keto-D,L-arginine (4) is not a substrate, but is an inhibitor of the three isozymes. Therefore, it appears that arginine binds to all of the NOS isozymes in an extended (E-like) conformation. None of the compounds exhibits time-dependent inhibition of NOS, but they are competitive reversible inhibitors. Based on the earlier report that NW-propyl-L-arginine is a highly selective nNOS inhibitor (Zhang, H. Q.; Fast, W.; Marletta, M.; Martasek, P.; Silverman, R. B. J. Med. Chem. 1997, 40, 3869), (E)-N-omega-propyl-3,4-didehydro-D,L-arginine (5) was synthesized, but it was shown to be weakly potent and only a mildly selective inhibitor of NOS. Imposing conformational rigidity on an arginine backbone does not appear to be a favorable approach for selective NOS inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00029-2

文献信息

• Pharmaceutical compositions of
  申请人：SmithKline Corporation

  公开号：US04067978A1

  公开（公告）日：1978-01-10

  Cephalosporins with a .alpha.-amino-(ureidophenyl)acetamido substituent at position 7 are prepared by acylation of a 7-aminocephalosporin with a derivative of .alpha.-amino-p(or m)-ureidophenylacetic acid. These compounds are antibacterial agents.

  在第7位具有.alpha.-氨基-(脲基苯基)乙酰氨基取代基的头孢菌素，通过使用.alpha.-氨基-p（或m）-脲基苯乙酸的衍生物对7-氨基头孢菌素进行酰化反应制备而成。这些化合物是抗菌剂。
• Alpha-amino-alpha-(ureidophenyl)acetamidocephalosporins and their
  申请人：SmithKline Corporation

  公开号：US04067976A1

  公开（公告）日：1978-01-10

  Cephalosporins with a .alpha.-amino-(ureidophenyl)acetamido substituent at position 7 are prepared by acylation of a 7-aminocephalosporin with a derivative of .alpha.-amino-p(or m)-ureidophenylacetic acid. These compounds are antibacterial agents.

  在第7位上带有.alpha.-氨基-(尿苯)乙酰胺基取代基的头孢菌素是通过用.alpha.-氨基-p（或m）-尿苯乙酸衍生物对7-氨基头孢菌素进行酰化制备的。这些化合物是抗菌剂。
• .alpha.-AMINO-.alpha.-(UREIDOPHENYL)ACETAMIDOCEPHALOSPORINS AND THEIR
  申请人：SmithKline Corporation

  公开号：US04067977A1

  公开（公告）日：1978-01-10

  Cephalosporins with a .alpha.-amino-(ureidophenyl)acetamido substituent at position 7 are prepared by acylation of a 7-aminocephalosporin with a derivative of .alpha.-amino-p(or m)-ureidophenylacetic acid. These compounds are antibacterial agents.

  在第7位具有.alpha.-氨基-(尿素苯基)乙酰氨基取代基的头孢菌素，是通过用.alpha.-氨基-p（或m）-尿素苯乙酸衍生物对7-氨基头孢菌素进行酰化制备的。这些化合物是抗菌剂。
• Protected .alpha.-amino-.alpha.-ureido(thioureido)phenylacetic acids
  申请人：SmithKline Corporation

  公开号：US04091227A1

  公开（公告）日：1978-05-23

  Cephalosporins with a .alpha.-amino-(ureidophenyl)acetamido substituent at position 7 are prepared by acylation of a 7-aminocephalosporin with a derivative of .alpha.-amino-p(or m)-ureidophenylacetic acid. These compounds are antibacterial agents.

  在第7位具有.alpha.-氨基-(尿素苯基)乙酰氨基取代基的头孢菌素，是通过用.alpha.-氨基-p（或m）-尿素苯乙酸衍生物对7-氨基头孢菌素进行酰化制备的。这些化合物是抗菌剂。
• Aryl-Phenyl-Sulfonamide-Phenylene Compounds and Their Use
  申请人：Greig Iain Robert

  公开号：US20110190302A1

  公开（公告）日：2011-08-04

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain aryl-phenyl-sulfonamido-phenylene compounds of the following formula (I) (collectively referred to herein as “APSAP compounds”). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, in treatment, for example, of inflammation and/or joint destruction and/or bone loss; of disorders mediated by excessive and/or inappropriate and/or prolonged activation of the immune system; of inflammatory and autoimmune disorders, for example, rheumatoid arthritis, psoriasis, psoriatic arthritis, chronic obstructive pulmonary disease (COPD), atherosclerosis, inflammatory bowel disease, ankylosing spondylitis, and the like; of disorders associated with bone loss, such as bone loss associated with excessive osteoclast activity in rheumatoid arthritis, osteoporosis, cancer-associated bone disease, Paget's disease and the like, etc.; and of cancer, such as a haematological malignancy, a solid tumour, etc.

  本发明涉及治疗化合物领域，更具体地涉及以下公式（I）的某些芳基-苯基-磺酰胺基-苯基化合物（以下统称为“APSAP化合物”）。本发明还涉及包含这些化合物的制药组合物，以及这些化合物和组合物的使用，无论是在体外还是体内，用于治疗炎症和/或关节破坏和/或骨质流失；治疗由免疫系统过度和/或不适当和/或持续激活引起的疾病；治疗炎症和自身免疫性疾病，例如类风湿性关节炎、牛皮癣、银屑病性关节炎、慢性阻塞性肺疾病（COPD）、动脉粥样硬化、炎性肠病、强直性脊柱炎等；治疗与骨质流失有关的疾病，例如类风湿关节炎中过度破骨细胞活动引起的骨质流失、骨质疏松症、癌症相关骨病、帕吉特病等；以及治疗癌症，例如血液系统恶性肿瘤、实体瘤等。