2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide | 1050329-20-8

• 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: 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide
• 英文别名: DBMPP；2,3-Dibromo-1-phenyl-3-methyl-1-phosphacyclopentane-1-one；2,3-dibromo-3-methyl-1-phenyl-1λ5-phospholane 1-oxide
• CAS: 1050329-20-8
• 化学式: C₁₁H₁₃Br₂OP
• 分子量: 352.005
• InChiKey: WEUOJWFXBQJEJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基-丁烯 在 manganese(IV) oxide 、 水 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide
  参考文献：
  名称：

  Novel Multiple Type Molecular Targeted Antitumor Agents: Preparation and Preclinical Evaluation of Low-Molecular-Weight Phospha Sugar Derivatives

  摘要：

  Phospha sugar derivatives of 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide and 2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide were synthesized from 2-phospholenes and evaluated by in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide method against leukemia cell lines, and then characterized by cell cycle analysis, Western blot analysis, and molecular docking simulation. Phospha sugar derivatives were revealed to be potential antitumor agents against leukemia cell lines such as U937 and K562. Cell cycle analysis indicated that phospha sugar derivatives induced apoptoses. Western blot analyses against U937 showed that phospha sugar derivatives regulate many mitotic regulators in cell cycle. Results of molecular docking simulation suggested that phospha sugar derivatives enter the pockets present in cell cycle and apoptosis-related proteins.

  DOI：

  10.1080/10426507.2014.993758

文献信息

• Preparation And Characterization Of Phospholanes And Phospha Sugars As Novel Anti-Cancer Agents
  作者：Satoru Ito、Mitsuji Yamashita、Taishi Niimi、Michio Fujie、Valluru Krishna Reddy、Hirono Totsuka、Buchammagari Haritha、Kasthuraiah Maddali、Satoki Nakamura、Kazuhide Asai、Takuya Suyama、Junko Yamashita、Yukiko Iguchi、Gang Yu、Tatsuo Oshikawa

  DOI：10.1515/hc.2009.15.1.23

  日期：2009.1

  2-bromo-3-hydroxy-l-phenylphospholane 1-oxides being prepared from l-phenyl-2-phospholene 1-oxide. Alternatively, the epoxides were also prepared by the epoxidation of the 2-phospholene with peroxides such as sodium peroxide and hydrogen peroxide. The reactivity and regioselectivity for the reaction of erythro and threo forms of the 2,3-epoxides with nucleophiles were investigated by using amines, and the reaction afforded

  2,3-环氧-1-苯基磷烷1-氧化物的非对映异构赤型和苏型由1-苯基-2-制备的2-溴-3-羟基-1-苯基磷烷1-氧化物的苏式和赤式形式合成磷烯 1-氧化物。或者，还通过2-磷烯与过氧化物例如过氧化钠和过氧化氢的环氧化来制备环氧化物。使用胺类研究了赤型和苏型 2,3-环氧化物与亲核试剂反应的反应性和区域选择性，反应得到 2-氨基-3-羟基-1-苯基膦烷 1-氧化物，对应于磷糖 N-糖苷。2,3-Dibromo-3-methyl-1-phenylphospholane 1-oxides 首先由 3-methyl-1-phenyl-2-phospholene 1-oxide 制备。制备的磷杂环戊烷或磷酸糖通过 ΜΤΓ (3-(4,
• Synthesis of Some 1-Aryl-2,3-dibromophospholanes as Novel Anti-Cancer Agents
  作者：Manabu Yamada,、Kazuhide Asai,、Junko Yamashita,、Takuya Suyama,、Taishi Niimi,、Kasthuraiah Maddali,、Michio Fujie,、Satoki Nakamura,、Motohiko Kimura,、Yasutaka Tanaka,、Mitsuo Toda,、Mitsuji Yamashita,

  DOI：10.1515/hc.2010.16.2-3.173

  日期：2010.6

  Novel phosphorus heterocyclic compounds, 3-methyl-l-(3-bromophenyl as well as some 3-substituted phenyl)-2phospholene 1-oxides (Id as well as lb, lc, and If), were synthesized from l-phenyl-2-phospholene 1-oxide la via 3methyl-l-(3-nitrophenyl)-2-phospholene 1-oxide (lb). l-(4-Bromophenyl)-2-phospholene le was prepared by Grignard coupling reaction of l-chloro-3-methyl-2-phospholene 1-oxide with 4

  新型磷杂环化合物，3-甲基-1-（3-溴苯基以及一些 3-取代苯基）-2磷烯 1-氧化物（Id 以及 lb、lc 和 If），由 l-苯基-2 合成-磷烯1-氧化物1a经由3甲基-1-(3-硝基苯基)-2-磷烯1-氧化物(lb)。1-(4-溴苯基)-2-磷烯le是通过1-氯-3-甲基-2-磷烯1-氧化物与4-溴苯基溴化镁的格利雅偶联反应制备的。2,3-Df溴3-甲基-1-芳基膦烷1-氧化物(2a-2e)通过溴与2-磷烯lale的C=C双键的加成反应制备。MTT体外方法评价1-芳基-磷泳道2的苯基对观察到的抗U937白血病细胞系抗增殖作用的取代作用表明，2,3-二溴3-甲基-1-(4-溴苯基)磷烷 (2e) 是 2 中最活跃的。
• Research on Phospha Sugar Analogues to Develop Novel Multiple Type Molecular Targeted Antitumor Drugs Against Various Types of Tumor Cells
  作者：Reiko Makita、Mitsuji Yamashita、Michio Fujie、Mayumi Yamaoka、Keita Kiyofuji、Manabu Yamada、Junko Yamashita、Kenji Tsunekawa、Kazuhide Asai、Takuya Suyama、Mitsuo Toda、Yasutaka Tanaka、Haruhiko Sugimura、Yasuhiro Magata、Kazunori Ohnishi、Satoki Nakamura

  DOI：10.1080/10426507.2012.744016

  日期：2013.1.1

  The synthesis and antitumor activity evaluation of new branched phospha sugars, especially deoxybromophospha sugar derivatives or bromophospholanes of 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (DBMPP: 3) and 2,3,4-tribromo-3-methyl-1- phenylphospholane 1-oxide (TBMPP: 4), against various types of leukemia cell lines as well as the results of the mechanistic studies for characterizing and developing the novel multiple type molecular targeted antitumor agents are reported in this paper. DBMPP and TBMPP were prepared from 1-phenyl-3-methyl-2-phospholene 1-oxide (1). The isomer mixture of phospha sugars prepared were evaluated as novel antitumor agents by MTT in vitro method. DBMPP and TBMPP were characterized by flow cytometry and Western blot analysis and were revealed to be potential antitumor agents against leukemia cell lines of K562 (one type of leukemia cell lines of CML) and U937 (one type of leukemia cell lines of AML) as well as against the various types of leukemia cell lines and also against solid tumor cell lines of stomach, skin, and lung cancers by MTT evaluation and observation by a handstand phase-contrast microscope. The results of the flow cytometry indicated that the mechanism of apoptosis induced by phospha sugar derivatives not only to tumor cells of leukemia cell lines of U937 but also to tumor cells of various kinds of leukemia cell lines selectively to decrease the tumor cell viability of various kinds of leukemia cell lines. The Western blot analyses for phospha sugar DBMPP against U937 leukemia cell lines showed that the phospha sugar affected on the expressions of the factors of cell cycles in the manners of suppressing the expression of the accelerator factors of cell cycles of tumor cells and enhancing the expression of suppressor factors of cell cycles of tumor cells by the medications of phospha sugars. TBMPP enhanced the expression of IER5 and then suppressed the expression of Cdc25B, which is the common factor to accelerate the cell cycles of various kinds of tumor cells. Therefore, suppression of the expression of Cdc25B by TBMPP implies that the branched deoxybromophospha sugar derivatives might be novel and potential multiple type molecular targeted antitumor agents against various kinds of tumor cell lines.
• Research and Development of Phospha Sugar Anti-cancer Agents with Anti-leukemic Activity
  作者：Junko Yamashita,、Takuya Suyama,、Kazuhide Asai,、Manabu Yamada,、Taishi Niimi,、Michio Fujie,、Satoki Nakamura,、Kazunori Ohnishi,、Mitsuji Yamashita,

  DOI：10.1515/hc.2010.16.2-3.89

  日期：2010.6
• Novel Multiple Type Molecular Targeted Antitumor Agents: Preparation and Preclinical Evaluation of Low-Molecular-Weight Phospha Sugar Derivatives
  作者：Reiko Makita、Mitsuji Yamashita、Mayumi Yamaoka、Michio Fujie、Satoki Nakamura、Tatsuo Oshikawa、Junko Yamashita、Manabu Yamada、Kazuhide Asai、Takuya Suyama、Mitsuru Kondo、Hiroko Hasegawa、Yoshimitsu Okita、Kazutaka Hirakawa、Mitsuo Toda、Kazunori Ohnishi、Haruhiko Sugimura

  DOI：10.1080/10426507.2014.993758

  日期：2015.6.3

  Phospha sugar derivatives of 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide and 2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide were synthesized from 2-phospholenes and evaluated by in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide method against leukemia cell lines, and then characterized by cell cycle analysis, Western blot analysis, and molecular docking simulation. Phospha sugar derivatives were revealed to be potential antitumor agents against leukemia cell lines such as U937 and K562. Cell cycle analysis indicated that phospha sugar derivatives induced apoptoses. Western blot analyses against U937 showed that phospha sugar derivatives regulate many mitotic regulators in cell cycle. Results of molecular docking simulation suggested that phospha sugar derivatives enter the pockets present in cell cycle and apoptosis-related proteins.