benzyl (S)-(2-phenyl-1-(1H-tetrazol-5-yl)ethyl)carbamate | 47365-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S)-(2-phenyl-1-(1H-tetrazol-5-yl)ethyl)carbamate
• 英文别名: [2-phenyl-1-(1H-tetrazol-5-yl)-ethyl]-carbamic acid benzyl ester；L-5-(α-Benzyloxycarbonylamino-β-phenyl-ethyl)-1H-tetrazol；benzyl N-[(1S)-2-phenyl-1-(2H-tetrazol-5-yl)ethyl]carbamate
• CAS: 47365-05-9
• 化学式: C₁₇H₁₇N₅O₂
• 分子量: 323.354
• InChiKey: RMWHZSMQANMGGW-HNNXBMFYSA-N

物化性质

• 熔点：
  177-178 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (S)-(2-phenyl-1-(1H-tetrazol-5-yl)ethyl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Glycosylation mediated—BAIL in aqueous solution

  摘要：

  The use of Bronsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.009
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨腈 在 sodium azide 、 zinc dibromide 作用下， 以 水 、 异丙醇 为溶剂， 反应 16.0h， 以91%的产率得到benzyl (S)-(2-phenyl-1-(1H-tetrazol-5-yl)ethyl)carbamate
  参考文献：
  名称：

  WO2007/8848

  摘要：

  公开号：

文献信息

• LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates
  作者：Arik A. Zur、Huan-Chieh Chien、Evan Augustyn、Andrew Flint、Nathan Heeren、Karissa Finke、Christopher Hernandez、Logan Hansen、Sydney Miller、Lawrence Lin、Kathleen M. Giacomini、Claire Colas、Avner Schlessinger、Allen A. Thomas

  DOI：10.1016/j.bmcl.2016.09.001

  日期：2016.10

  demonstrated weak substrate activity, its structure–activity relationship (SAR) was further explored by synthesis and testing of HA derivatives of other LAT1 amino acid substrates (i.e., Tyr, Leu, Ile, and Met). The potential for a false positive in the trans-stimulation assay caused by parent amino acid was evaluated by conducting compound stability experiments for both HA-Leu and the corresponding methyl ester

  大型中性氨基酸转运蛋白1（LAT1）是一种溶质载体蛋白，主要位于血脑屏障（BBB）中，具有将药物输送到大脑的潜力。作为肿瘤新陈代谢需求增加的一部分，它在癌细胞中也被上调。以前，已经证明氨基酸前药是通过LAT1转运的。与天然氨基酸衍生的羧酸相比，羧酸类生物甾醇可能提供具有改变的物理化学和药代动力学特性的前药，从而使药物的大脑或肿瘤水平更高和/或毒性更低。考察了用四唑，酰基磺酰胺和异羟肟酸（HA）生物等排代物取代苯丙氨酸的羧酸的效果。使用顺式抑制和抑制作用对化合物作为LAT1底物的能力进行了测试反刺激细胞测定。由于HA-Phe具有弱的底物活性，因此通过合成和测试其他LAT1氨基酸底物（即Tyr，Leu，Ile和Met）的HA衍生物，进一步探索了其结构-活性关系（SAR）。通过对HA-Leu和相应的甲酯衍生物进行化合物稳定性实验，评估了由亲本氨基酸引起的反式刺激试验中假阳性的可能性。我们得出的结
• Monomethylvaline Compounds Having Phenylalanine Carboxy Modifications at the C-Terminus
  申请人：Doronina Svetlana O.

  公开号：US20090111756A1

  公开（公告）日：2009-04-30

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) having a carboxylic acid equivalent at the C-terminal phenylalanine were prepared and attached to ligands through various linkers, including maleimidocaproyl-val-cit-PAB. The resulting ligand drug conjugates were active in vitro and in vivo.

  具有C-末端苯丙氨酸羧基酸等效物的MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物已经制备，并通过各种连接剂（包括maleimidocaproyl-val-cit-PAB）连接到配体上。 结果得到的配体药物结合物在体外和体内均具有活性。
• METHODS OF USING MONOMETHYLVALINE COMPOSITIONS HAVING PHENYLALANINE CARBOXY MODIFICATIONS AT THE C-TERMINUS
  申请人：Seattle Genetics, Inc.

  公开号：US20150044238A1

  公开（公告）日：2015-02-12

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) having a carboxylic acid equivalent at the C-terminal phenylalanine were prepared and attached to ligands through various linkers, including maleimidocaproyl-val-cit-PAB. The resulting ligand-drug conjugates were active in vitro and in vivo in inhibiting cell proliferation and are represented by the general structure of L v -[(LU) 0-1 -(D) 1-4 ] p wherein L- is Ligand unit; LU is a Linker unit (LU); v is 1; p is an number ranging from about 1 to about 20; and D is a drug moiety having the formula: wherein the moiety —N(R 9 )Z 1 is a phenylalanine bioisostere, wherein Z 1 is —CH(R 10 )Z 2 so that the phenylalanine bioisostere has the structure of Formula A: and wherein the substituents R 2 -R 10 , X 1 and Z 2 are as defined.

  制备了具有C端苯丙氨酸羧酸等效物的MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物，并通过各种连接剂将其连接到配体上，包括maleimidocaproyl-val-cit-PAB。所得的配体-药物偶联物在体外和体内抑制细胞增殖方面具有活性，并由以下一般结构表示：Lv-[(LU)0-1-(D)1-4]p，其中L-是配体单元；LU是连接单元（LU）；v为1；p为约1至约20的数字；D是具有以下公式的药物基团：其中，—N（R9）Z1基团是苯丙氨酸生物同构体，其中Z1是—CH（R10）Z2，以便苯丙氨酸生物同构体具有A式结构；其中取代基R2-R10、X1和Z2如定义。
• A New Chiral Synthesis of a Bicyclic Enedione Containing a Seven-Membered Ring Mediated by a Combination of Chiral Amine and Brønsted Acid
  作者：Kohei Inomata、Takashi Nagamine、Yasuyuki Endo

  DOI：10.3987/com-08-s(n)81

  日期：——
• Microwave-Assisted One-Pot Tandem Reactions for Direct Conversion of Primary Alcohols and Aldehydes to Triazines and Tetrazoles in Aqueous Media
  作者：Jiun-Jie Shie、Jim-Min Fang

  DOI：10.1021/jo0625352

  日期：2007.4.1

  A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford high yields of the corresponding triazines and tetrazoles, including the alpha-amino- and dipeptidyl tetrazoles in high optical purity.