氨基-(3-硝基-苯基)-乙酸 | 30077-08-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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
• 中文名称: 氨基-(3-硝基-苯基)-乙酸
• 中文别名: (S)-间硝基苯甘氨酸；3-硝基-DL-苯甘氨酸
• 英文名称: 2-amino-2-(3-nitrophenyl)acetic acid
• 英文别名: amino(3-nitro-phenyl)acetic acid；d-α-amino-m-nitrophenylacetic acid；2-azaniumyl-2-(3-nitrophenyl)acetate
• CAS: 30077-08-8
• 化学式: C₈H₈N₂O₄
• mdl: MFCD04966788
• 分子量: 196.163
• InChiKey: RJMYTHGQVJWWJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	D-(-)-α-(m-nitrophenyl)glycine	4885-81-8	C8H8N2O4	196.163

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  甲基氨基(3-硝基苯基)乙酸酯	methyl 2-amino-2-(3-nitrophenyl)acetate	687631-80-7	C9H10N2O4	210.189
  氨基(3-氨基苯基)乙酸	amino-(3-amino-phenyl)-acetic acid	90271-39-9	C8H10N2O2	166.18
  ——	D-2-tert-butoxycarbonylamino-2-(3-nitrophenyl)-acetic acid	54895-27-1	C13H16N2O6	296.28
  ——	N-(benzyloxycarbonyl)-D-2-amino-2-(3-nitrophenyl)acetic acid	140460-47-5	C16H14N2O6	330.297
  alpha-羟基-3-硝基苯乙酸	3-nitromandelic acid	42164-79-4	C8H7NO5	197.147
  ——	methyl 2-((tert-butoxycarbonyl)amino)-2-(3-nitrophenyl)acetate	188586-91-6	C14H18N2O6	310.307
  ——	tert-butyl (2-hydroxy-1-(3-nitrophenyl)ethyl)carbamate	——	C13H18N2O5	282.296
  ——	2-((tert-butoxycarbonyl)amino)-2-(3-nitrophenyl)ethyl methanesulfonate	140373-23-5	C14H20N2O7S	360.388

反应信息

• 作为反应物：
  描述：

  氨基-(3-硝基-苯基)-乙酸 在 palladium on activated charcoal 氢气 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 生成 Nα-Boc-m-cyanamido-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
• 作为产物：
  描述：

  2-氨基-2-苯基乙酸 在 硫酸 、 硝酸 作用下， 反应 1.5h， 以64%的产率得到氨基-(3-硝基-苯基)-乙酸
  参考文献：
  名称：

  Design, synthesis and biological evaluation of non-covalent AmpC β-lactamases inhibitors

  摘要：

  Bacterial resistance represents a worldwide emergency threatening the efficacy of all available antibiotics. Among the several resistance mechanisms developed by bacteria, beta-lactamase enzymes (BLs), which are able to inactivate most beta-lactam core antibiotics, represent a key target to block, thus prolonging antibiotics half-life. Several approaches aimed at inhibiting beta-lactamases have been so far undertaken, mainly involving beta-lactam-like or covalent inhibitors. Applying a structure-based de novo design approach, we recently discovered a novel, non-covalent and competitive inhibitor of AmpC beta-lactamase: lead 1. It has a K-i of 1 mu M, a ligand efficiency of 0.38 kcal mol(-1) and lead-like physical properties. Moreover, it reverts resistance to ceftazidime in bacterial pathogens expressing AmpC and does not up-regulate beta-lactamases expression in cell culture. Its features make it a good candidate for chemical optimization: starting from lead 1 crystallographic complex with AmpC, 11 analogs were designed to complement additional AmpC sites, then synthesized and tested against clinically resistant pathogens. While the new inhibitors maintain similar in vitro activity as the starting lead, some of them, in biological assays, extert a higher potency showing improved synergic activity with ceftazidime in resistant clinically isolated strains.

  DOI：

  10.1007/s00044-017-1809-x

文献信息

• Antibacterial 3-(5-tetrazolyl) penam compounds
  申请人：Pfizer Inc.

  公开号：US04115385A1

  公开（公告）日：1978-09-19

  Certain novel 6-acylamino-2,2-dimethyl-3-(5-tetrazolyl)penam derivatives, and salts thereof; their use as broad-spectrum antibacterial agents; and methods for their preparation. Their preparation comprises acylation of the novel intermediate, 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam or simple derivatives thereof, followed, in some cases, by further transformations of the 6-acylamino group or by removal of a protecting group from the 5-tetrazolyl moiety. Process for the preparation of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, simple derivatives thereof and intermediates therefor.

  某些新型6-酰氨基-2,2-二甲基-3-(5-四唑基)佩纳姆衍生物及其盐；它们作为广谱抗菌剂的用途；以及它们的制备方法。它们的制备包括对新型中间体6-氨基-2,2-二甲基-3-(5-四唑基)佩纳姆或其简单衍生物进行酰化，然后在某些情况下，通过进一步转化6-酰氨基基团或去除5-四唑基团的保护基来进行。制备6-氨基-2,2-二甲基-3-(5-四唑基)佩纳姆、其简单衍生物及其中间体的方法。
• Antibacterial 3-(5-tetrazolyl)penam compounds
  申请人：Pfizer Inc.

  公开号：US04143039A1

  公开（公告）日：1979-03-06

  Certain novel 6-acylamino-2,2-dimethyl-3-(5-tetrazolyl)penam derivatives, and salts thereof; their use as broad-spectrum antibacterial agents; and methods for their preparation. Their preparation comprises acylation of the novel intermediate, 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam or simple derivatives thereof, followed, in some cases, by further transformations of the 6-acylamino group or by removal of a protecting group from the 5-tetrazolyl moiety. Process for the preparation of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, simple derivatives thereof and intermediates therefor.

  某些新型6-酰氨基-2,2-二甲基-3-(5-四唑基)佩纳姆衍生物及其盐；它们作为广谱抗菌剂的用途；以及它们的制备方法。它们的制备包括对新型中间体6-氨基-2,2-二甲基-3-(5-四唑基)佩纳姆或其简单衍生物进行酰化，然后，在某些情况下，通过进一步转化6-酰氨基基团或去除5-四唑基团的保护基来进行。制备6-氨基-2,2-二甲基-3-(5-四唑基)佩纳姆、其简单衍生物及其中间体的方法。
• [EN] GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] ANTAGONISTES DES RÉCEPTEURS DE L'HORMONE DE LIBÉRATION DES GONADOTROPHINES, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：SK CHEMICALS CO LTD

  公开号：WO2013129879A1

  公开（公告）日：2013-09-06

  The present invention provides gonadotropin releasing hormone receptor antagonists and the pharmaceutical composition comprising the same, which can be useful in preventing or treating a sex hormone-related disease such as endometriosis, amenorrhea, irregular menstruation, uterine myoma, uterine fibroids, polycystic ovarian disease, lupus erythematous, hypertrichosis, precocious puberty, short stature, acne, alopecia, gonadal steroid-dependent neoplasms, gonadotropin-producing pituitary adenoma, sleep apnea, irritable bowel syndrome, premenstrual syndrome, benign prostatic hyperplasia, contraception, and infertility, as well as Alzheimer disease.

  本发明提供了促性腺激素释放激素受体拮抗剂及包括其的药物组合物，可用于预防或治疗与性激素相关的疾病，如子宫内膜异位症、闭经、月经不调、子宫肌瘤、子宫肌瘤、多囊卵巢综合征、红斑狼疮、多毛症、性早熟、身材矮小、痤疮、脱发、性腺类固醇依赖性肿瘤、促性腺激素产生性垂体腺瘤、睡眠呼吸暂停、肠易激综合征、经前综合征、良性前列腺增生、避孕和不孕症，以及阿尔茨海默病。
• GONADOTROPIN RELEASING HORMONE RECEPTOR ANTAGONISTS, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：SK CHEMICALS CO., LTD.

  公开号：US20150166558A1

  公开（公告）日：2015-06-18

  Disclosed are a gonadotropin releasing hormone receptor antagonist and a pharmaceutical composition including the same, which can be useful in preventing or treating a sex hormone-related disease such as endometriosis, amenorrhea, irregular menstruation, uterine myoma, uterine fibroids, polycystic ovarian disease, lupus erythematous, hypertrichosis, precocious puberty, short stature, acne, alopecia, gonadal steroid-dependent neoplasms, gonadotropin-producing pituitary adenoma, sleep apnea, irritable bowel syndrome, premenstrual syndrome, benign prostatic hyperplasia, contraception, and infertility, as well as Alzheimer disease.

  揭示了一种促性腺激素释放激素受体拮抗剂和包括该拮抗剂的药物组合物，可用于预防或治疗与性激素相关的疾病，如子宫内膜异位症、闭经、月经不调、子宫肌瘤、子宫纤维瘤、多囊卵巢综合征、红斑狼疮、多毛症、性早熟、身材矮小、痤疮、脱发、性腺类固醇依赖性肿瘤、促性腺激素产生垂体腺瘤、睡眠呼吸暂停、肠易激综合征、经前综合征、良性前列腺增生、避孕和不孕症，以及阿尔茨海默病。
• [EN] ARYL-PHENYL-SULFONAMIDE-PHENYLENE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS ARYL-PHÉNYL-SULFONAMINO-PHÉNYLÈNE ET LEURS UTILISATIONS
  申请人：PIMCO 2664 LTD

  公开号：WO2010032010A1

  公开（公告）日：2010-03-25

  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.

  本发明通常涉及治疗化合物领域，更具体地涉及以下式(I)的某些芳基苯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药物组合物，以及这些化合物和组合物在体内外的使用，例如用于治疗炎症和/或关节破坏和/或骨质流失；过度和/或不适当和/或持续激活免疫系统的疾病；炎症性和自身免疫性疾病，例如类风湿关节炎、牛皮癣、银屑病性关节炎、慢性阻塞性肺病（COPD）、动脉粥样硬化、炎症性肠病、强直性脊柱炎等；与骨质流失相关的疾病，例如类风湿性关节炎中与过度破骨细胞活性相关的骨质流失、骨质疏松症、癌症相关骨病、帕吉特病等；以及癌症，如血液系统恶性肿瘤、实体肿瘤等。