isocyanatomethyl-carbamic acid 9h-fluoren-9-ylmethyl ester | 611198-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: isocyanatomethyl-carbamic acid 9h-fluoren-9-ylmethyl ester
• 英文别名: Carbamic acid, (isocyanatomethyl)-, 9H-fluoren-9-ylmethyl ester；9H-fluoren-9-ylmethyl N-(isocyanatomethyl)carbamate
• CAS: 611198-15-3
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: HHCAFEAKBZJVMO-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  479.0±28.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isocyanatomethyl-carbamic acid 9h-fluoren-9-ylmethyl ester 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成
  参考文献：
  名称：

  Patil, Basanagoud S.; Suresh Babu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1721 - 1728

  摘要：

  DOI：
• 作为产物：
  描述：

  Fmoc-Gly-NH2 在 吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 为溶剂， 生成 isocyanatomethyl-carbamic acid 9h-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Facile incorporation of urea pseudopeptides into protease substrate analogue inhibitors

  摘要：

  A new procedure that employs a one-pot, oxidative Hofmann rearrangement to incorporate a urea linkage into peptide backbones is detailed herein. This methodology was used to replace the scissile peptide bonds of [Leu(5)]enkephalin and a hexapeptide HIV-1 protease substrate. The [Leu(5)]enkephalin analogue was found to inhibit cleavage of hippurylhistidylleucine (HHL) by porcine kidney angiotensin-converting enzyme (PK-ACE) with a 0.88 mM IC50 value, comparable to the Michaelis constant of [Leu(5)]enkephalin with the same enzyme. The HIV-1 protease substrate analogue was shown to inhibit HIV-1 protease with an IC50 = 34muM. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.092

文献信息

• New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
  作者：Vommina V. Sureshbabu、H. S. Lalithamba、N. Narendra、H. P. Hemantha

  DOI：10.1039/b920290k

  日期：——

  Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved.

  使用肽偶联剂，EDC和 HBTU描述。该程序高效，实用并且适用于多种羧酸，包括ñ保护的氨基酸。使用相同的试剂，还可以从酸一锅合成尿素，二肽基脲酯和氨基甲酸酯。
• Characterization of Nα-Fmoc-protected ureidopeptides by electrospray ionization tandem mass spectrometry (ESI-MS/MS): differentiation of positional isomers
  作者：M. Ramesh、B. Raju、R. Srinivas、V. V. Sureshbabu、N. Narendra、B. Vasantha

  DOI：10.1002/jms.1862

  日期：2010.12

  (9H‐fluoren‐9‐yl)methyl cation (C14H11+) from FmocNH = CHR+. In addition, characteristic immonium ions are also observed. The deprotonated ureidopeptide acids dissociate differently from the protonated ureidopeptides. The [M − H]− ions of ureidopeptide acids undergo a McLafferty‐type rearrangement followed by the loss of CO2 to form an abundant [M − H − Fmoc + H]− which is absent for protonated ureidopeptides

  四对脲肽位置异构体，FmocNH-CH（R 1）-φ（NH-CO-NH）-CH（R 2）-OY和FmocNH-CH（R 2）-φ（NH-CO-NH）- CH（R 1）-OY（Fmoc = [（9-芴基甲基）氧基]羰基; R 1 = H，烷基; R 2 =烷基，H和Y = CH 3 / H），已通过两种方法进行了表征和区分正离子和负离子电喷雾电离（ESI）离子阱串联质谱（MS / MS）。在MS注意到主要分段/所有这些化合物的MS是由于 Ñ  CH（R） Ñ 键裂解形成特征性的N和C端碎片离子。N端的甘氨酸衍生的质子化的尿苷肽酸在m / z 240时形成质子化的（9H-芴-9-9）甲基氨基甲酸酯离子，而相应的酯则不存在。在N端衍生自甘氨酸的尿苷肽中发现的另一个有趣的片段化是中间片段离子FmocNH = CH 2 +（m / z 252）导致的61个单位的异常丢失。一种涉及离子中性络合物以及NH
• 3-Substituted-4-Oxo-3,4-Dihydro-Imidazo[5,1-d][1,2,3,5-Tetrazine-8-Carboxylic Acid Amides and Their Use
  申请人：Stevens Malcolm Francis Graham

  公开号：US20100286088A1

  公开（公告）日：2010-11-11

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 3-substituted-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (collectively referred to herein as 3TM 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, to inhibit cell proliferation, and in the treatment of proliferative disorders such as cancer, etc., and methods of preparing such compounds.

  本发明涉及治疗化合物领域，更具体地涉及某些3-取代-4-氧代-3,4-二氢咪唑[5,1-d][1,2,3,5]四嗪-8-羧酸酰胺（统称为3TM化合物）。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物来抑制细胞增殖，在治疗增生性疾病如癌症等方面的应用，以及制备这种化合物的方法。
• 3-substituted-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5-tetrazine-8-carboxylic acid amides and their use
  申请人：Stevens Malcolm Francis Graham

  公开号：US08450479B2

  公开（公告）日：2013-05-28

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 3-substituted-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (collectively referred to herein as 3TM 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, to inhibit cell proliferation, and in the treatment of proliferative disorders such as cancer, etc., and methods of preparing such compounds.

  本发明涉及治疗化合物领域，更具体地涉及某些3-取代-4-氧代-3,4-二氢咪唑[5,1-d][1,2,3,5]四嗪-8-羧酸酰胺（统称为3TM化合物）。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物来抑制细胞增殖，治疗增殖性疾病如癌症等，以及制备这种化合物的方法。
• 3-Substituted-4-Oxo-3,4-Dihydro-Imidazo[5,1-d]1,2,3,5-Tetrazine-8-Carboxylic Acid Amides and Their Use
  申请人：Pharminox Limited

  公开号：US20130338104A1

  公开（公告）日：2013-12-19

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 3-substituted-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (collectively referred to herein as 3TM 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, to inhibit cell proliferation, and in the treatment of proliferative disorders such as cancer, etc., and methods of preparing such compounds.

  本发明涉及治疗化合物领域，更具体地涉及某些3-取代-4-氧代-3,4-二氢咪唑[5,1-d][1,2,3,5]四唑-8-羧酸酰胺（以下统称为3TM化合物）。本发明还涉及包含这种化合物的制药组合物，以及在体内外使用这种化合物和组合物来抑制细胞增殖，治疗增生性疾病如癌症等的用途，以及制备这种化合物的方法。